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[ CAS No. 1187836-86-7 ] {[proInfo.proName]}

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Chemical Structure| 1187836-86-7
Chemical Structure| 1187836-86-7
Structure of 1187836-86-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1187836-86-7 ]

CAS No. :1187836-86-7 MDL No. :MFCD20039163
Formula : C5H6BrNOS Boiling Point : -
Linear Structure Formula :- InChI Key :MQMFHTSXMPGVBI-UHFFFAOYSA-N
M.W : 208.08 Pubchem ID :58127549
Synonyms :

Calculated chemistry of [ 1187836-86-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.91
TPSA : 61.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.55
Log Po/w (MLOGP) : 0.36
Log Po/w (SILICOS-IT) : 3.04
Consensus Log Po/w : 1.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.757 mg/ml ; 0.00364 mol/l
Class : Soluble
Log S (Ali) : -2.43
Solubility : 0.778 mg/ml ; 0.00374 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.888 mg/ml ; 0.00427 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.82

Safety of [ 1187836-86-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1187836-86-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1187836-86-7 ]

[ 1187836-86-7 ] Synthesis Path-Downstream   1~50

  • 1
  • methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate [ No CAS ]
  • [ 1187836-86-7 ]
YieldReaction ConditionsOperation in experiment
77% With methanol; lithium borohydride In tetrahydrofuran at 5 - 20℃; 2 Preparation of (2-bromo-5-methyl-1 ,3-thiazol-4-yl)methanolTo a stirred solution of methyl 2-bromo-5-methyl-1 ,3-thiazole-4-carboxylate (2.89 g, 12.26 mmol, 1 eq.) in 120 ml dry THF cooled to 5ºC, was added LiBH4 (2M in THF, 12.26 ml, 24.53 mmol, 2 eq.) followed by MeOH (0.994 ml, 24.53 mmol, 2 eq.). The reaction was allowed to warm to r.t. and was stirred for further 18 hrs. The reaction was quenched by addition of sat. aqueous NH4CI and diluted with DCM. The aqueous layer was extracted with DCM, and the organic layers combined, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel to (2-bromo-5-nnethyl-1 ,3-thiazol-4- yl)methanol (2.07 g, 77 % yield) as a white solid. HPLC/MS : m/z = 209 (M+H) ; logP(HCooH) = 1.10
56% With diisobutylaluminium hydride In tetrahydrofuran at 0℃; for 3h; 13 (2-Bromo-5-methylthiazol-4-yI)methanol A solution of methyl 2-bromo-5-methylthiazole-4-carboxylate (1 .00 g, 4.24 mmol) in tetrahydrofuran (THF) (21 .18 mL) was cooled in ice bath. To this was added DIBAL-H(10.59 mL, 10.59 mmol) and stirred for2 h at 0°C. Additional DIBAL-H (8.47 mL, 8.47 mmol) was added and stirred for 1 h at 0°C. The reaction was quenched with 1 N HCI (l0mL) and stirred at 0°C for 15 minutes. Another iN HCI (lOmL) was added at ambient temperature and the aqueous layer was extracted with EtOAc (4X). The combined organic layers were washed with 1 N HCI, brine, dried with MgSO4 and concentrated to provide thetitle compound. (0.497 g, 56% yield). LC/MS m/z = 208/209 (M+H)+, 0.047 mm (ret. time).
44% With sodium tetrahydroborate; water In methanol at 0 - 20℃; for 3h;
With methanol; lithium borohydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; 106.106A (2-Bromo-5-methylthiazol-4-yl)methanol A solution of methyl 2-bromo-5-methylthiazole-4-carboxylate (1.00 g, 4.24 mmol) in tetrahydrofuran (20 mL) was cooled to 0 °C under nitrogen and treated with methanol (0.343 mL, 8.47 mmol) followed by lithium borohydride (0.185 g, 8.47 mmol), both added all at once. After 30 min, the cooling bath was removed and the resulting yellow solution was stirred at room temperature for 1.5 h. The reaction mixture was re- cooled at 0 °C, quenched with acetic acid (6 drops) and water (1 mL) and vigorously stirred for 10 min. The resulting mixture was then diluted with dichloromethane (200 mL), washed with saturated aqueous sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded the title compound (0.83 g, 94%) as a white solid which was used as such in the next step. HRMS(ESI): Calcd for C5H7BrNOS [M+H ]+ m/z 207.9426; found 207.9424. 1H NMR (CDCl3, 400 MHz): δ 4.63 (s, 2H), 2.42 (s, 3H), 2.30 (br s, 1H).

  • 2
  • [ 1187836-86-7 ]
  • [ 1187836-87-8 ]
YieldReaction ConditionsOperation in experiment
72% With pyridine; sulfurous dibromide In dichloromethane at 5 - 20℃; 3 To a stirred solution thionyl bromide (2.27 g, 10.94 mmol, 1.1 eq.) in 25 ml dry DCM , cooled to 5ºC, was added dropwise a solution of (2-bromo-5-methyl-1 ,3-thiazol-4-yl)methanol (2.07 g, 9.94 mmol, 1 eq. ) and pyridine (0.865 g, 10.94 mmol, 1.1 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the reaction warmed to room temperature and stirred 1.5 hr. 100 ml of water and 100 ml of DCM were added and stirring allowed for 2 mins. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by chromatography on silica gel to give 2- bromo-4-(bromomethyl)-5-methyl-1 ,3-thiazole (1.94 g, 72 % yield) as a white solid. HPLC/MS : m/z = 271 (M+H) ; logP(HCooH) = 2.64
40% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h;
  • 3
  • [ 1190235-92-7 ]
  • [ 1187836-86-7 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: (2-bromo-5-methyl-1,3-thiazol-4-yl)methyl acetate With water; sodium hydroxide In tetrahydrofuran; ethanol at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol; water 80d (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol (Example 80d) (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol To a mixed solution of the compound (1.2 g, 4.8 mmol) obtained in Example 80c in ethanol/tetrahydrofuran (v/v = 1/1, 4 mL) was added 2N aqueous sodium hydroxide solution (4.8 mL, 9.6 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane - hexane/ethyl acetate=50/50) to give the title compound (590 mg, 59%) as a colorless solid. 1H NMR (300 MHz, CHLOROFORM-d) δppm 2.41 (3 H, s), 4.63 (2 H, s) LCMS (ESI+) M+H+: 208.
  • 4
  • [ 37622-90-5 ]
  • [ 1187836-86-7 ]
  • [ 1190235-93-8 ]
YieldReaction ConditionsOperation in experiment
100% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; 80e ethyl 1-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methyl]-1H-pyrazole-4-carboxylate (Example 80e) ethyl 1-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methyl]-1H-pyrazole-4-carboxylate Under a nitrogen atmosphere at 0°C, to a solution (10 mL) of the compound (590 mg, 2.8 mmol) obtained in Example 80d, triphenylphosphine (970 m, 3.7 mmol) and ethyl 1H-pyrazole-4-carboxylate (480 mg, 3.4 mmol) in tetrahydrofuran was added diisopropyl azodicarboxylate (1.9 M toluene solution, 1.9 mL, 3.7 mmol), and the mixture was stirred at the same temperature for 2 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane - hexane/ethyl acetate=70/30) to give the title compound (940 mg, 100%) as a yellow oil. 1H NMR (300 MHz, CHLOROFORM-d) δppm 1.34 (3 H, t, J=7.1 Hz), 2.46 (3 H, s), 4.28 (2 H, q, J=7.1 Hz), 5.29 (2 H, s), 7.89 (1 H, s), 7.99 (1 H, s) LCMS (ESI+) M+H+: 330.
  • 5
  • [ 1187836-86-7 ]
  • (2-(3-(((6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzofuran-4-yl)oxy)methyl)phenyl)-5-methylthiazol-4-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide / 0.17 h / 1.5 Torr 1.2: 18 h / 23 °C / Inert atmosphere 2.1: sodium carbonate / toluene; ethanol / 0.17 h / Inert atmosphere 2.2: 3 h / 95 °C / Sealed tube; Inert atmosphere 3.1: 0.08 h 3.2: Inert atmosphere 3.3: 5 h / 20 °C / Inert atmosphere 4.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 18 h / 23 °C
  • 6
  • [ 1187836-86-7 ]
  • (3-(4-(((tert-butyldimethylsilyl)oxy)methyl)-5-methylthiazol-2-yl)phenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 0.17 h / 1.5 Torr 1.2: 18 h / 23 °C / Inert atmosphere 2.1: sodium carbonate / toluene; ethanol / 0.17 h / Inert atmosphere 2.2: 3 h / 95 °C / Sealed tube; Inert atmosphere
  • 7
  • [ 1187836-86-7 ]
  • 6-(4-((3-(4-(((tert-butyldimethylsilyl)oxy)methyl)-5-methylthiazol-2-yl)benzyl)oxy)-6-methoxybenzofuran-2-yl)-2-methoxyimidazo[2,1-b][1,3,4]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide / 0.17 h / 1.5 Torr 1.2: 18 h / 23 °C / Inert atmosphere 2.1: sodium carbonate / toluene; ethanol / 0.17 h / Inert atmosphere 2.2: 3 h / 95 °C / Sealed tube; Inert atmosphere 3.1: 0.08 h 3.2: Inert atmosphere 3.3: 5 h / 20 °C / Inert atmosphere
  • 8
  • [ 1187836-86-7 ]
  • [ 18162-48-6 ]
  • 2-bromo-4-([tert-butyl(dimethyl)silyl]oxy}methyl)-5-methyl-1,3-thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol In N,N-dimethyl-formamide for 0.166667h; Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 23℃; for 18h; Inert atmosphere; 106.106B 2-Bromo-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-methylthiazole In a 250 mL round-bottomed flask, a solution of crude (2-bromo-5- methylthiazol-4-yl)methanol (0.825 g, 3.96 mmol) in DMF (10 mL) was maintained under vacuum (2 mbar) for 10 min. The flask was then flushed with nitrogen and charged with imidazole (0.540 g, 7.93 mmol), followed by TBS-Cl (0.896 g, 5.95 mmol), both added in one portion. The resulting clear solution was stirred at 23 °C for 18 h before the DMF was evaporated under reduced pressure and the residue was partitioned with ethyl acetate-saturated aqueous sodium bicarbonate. The organic phase was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting oil was chromatographed on silica gel (3 x 12 cm, elution with toluene) to give the title compound (1.05 g, 82%) as a clear oil. LCMS (APCI): calcd for C11H21BrNOSSi [M+H]+ m/z 322.03, found 322.0. 1H NMR (CDCl3, 400 MHz): δ ppm 4.64 (s, 2H), 2.34 (s, 3H), 0.81 (s, 9H), 0.00 (s, 6H).
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; 46.1 To a solution of (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol (151 mg) in DMF (3 mL) was added imidazole (59 mg) and TBSCl (131 mg), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were then added saturated aqueous ammonium chloride solution and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and brine, dried over anhydrous sodium sulfate, filtered, and then concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 2-bromo-4-([tert-butyl(dimethyl)silyl]oxy}methyl)-5-methyl-1,3-thiazole.
  • 9
  • [ 1187836-86-7 ]
  • [ 824-94-2 ]
  • 2-bromo-4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% Stage #1: (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 20℃; for 2.5h; 13 2-Bromo-4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiazole A solution of (2-bromo-5-methylthiazol-4-yl)methanol (0.497 g, 2.389 mmol) in N,N15 dimethylformamide (DMF) (10 mL) under nitrogen was cooled to 0°C. 60% NaH (0.191 g,4.78 mmol) was added to the solution portion wise and stirred at 0 °C for 30 mm. A solution of 1-(chloromethyl)-4-methoxybenzene (0.561 g, 3.58 mmol) in N,Ndimethylformamide (DMF) (5 mL) was then added dropwise and reaction was allowed to warm to ambient temperature over 2.5 h. The reaction was then quenched with water andthe solvents were concentrated. The residue was dissolved in EtOAc and washed with water. The aqueous layer was extracted with EtOAc (3X) and the combined organics were washed with water, brine and dried with MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 0-20% EtOAc / hexanes to provide the title compound. (0.237 g, 26% yield). LC/MS m/z = 327/329 (M+H)+, 1 .05 mm (ret. time).
  • 10
  • [ 1187836-86-7 ]
  • (1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)(4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiazol-2-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C
  • 11
  • [ 1187836-86-7 ]
  • methyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiazol-2-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C
  • 12
  • [ 1187836-86-7 ]
  • benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiazol-2-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C
  • 13
  • [ 1187836-86-7 ]
  • benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(hydroxymethyl)-5-methylthiazol-2-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: ammonium cerium (IV) nitrate / acetonitrile / 1 h / 20 °C
  • 14
  • [ 1187836-86-7 ]
  • benzyl 3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: ammonium cerium (IV) nitrate / acetonitrile / 1 h / 20 °C 6.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 23 h / 20 °C
  • 15
  • [ 1187836-86-7 ]
  • 3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: ammonium cerium (IV) nitrate / acetonitrile / 1 h / 20 °C 6.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 23 h / 20 °C 7.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.5 h / 120 °C / Microwave irradiation
  • 16
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-N-(pyridin-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 3 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 21 h / 83 °C
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 3 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 21 h / 83 °C
  • 17
  • [ 1187836-86-7 ]
  • benzyl 3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiazol-2-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h
  • 18
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiazol-2-yl)-2,2-dimethylpropanoate [ No CAS ]
  • benzyl (R)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(((4-methoxybenzyl)oxy)methyl)-5-methylthiazol-2-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions
  • 19
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-(hydroxymethyl)-5-methylthiazol-2-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C
Multi-step reaction with 6 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C
  • 20
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
  • 21
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[2,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 3 h / Inert atmosphere
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 3 h / Inert atmosphere
  • 22
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[4,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / 18 h / 20 °C
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / 18 h / 20 °C
  • 23
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[4,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 26.5 h / Inert atmosphere
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 26.5 h / Inert atmosphere
  • 24
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[4,3-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-N-(pyridin-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 26.5 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 21 h / 83 °C
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 26.5 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 21 h / 83 °C
  • 25
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[3,2-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1Hbenzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
  • 26
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[3,2-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1Hbenzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 23 h / Inert atmosphere
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 23 h / Inert atmosphere
  • 27
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((R)-4-ethyl-1,1-dioxido-3,4-dihydro-2H-pyrido[3,2-b][1,4,5]oxathiazepin-2-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-N-(pyridin-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 23 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 21 h / 83 °C
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 23 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 21 h / 83 °C
  • 28
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
  • 29
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 2 h / Inert atmosphere
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 2 h / Inert atmosphere
  • 30
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-4,5-dihydropyrido[2,3-f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-N-(pyridin-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 2 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 18 h / 83 °C
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 2 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 18 h / 83 °C
  • 31
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
  • 32
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere
  • 33
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-N-(pyridin-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 18 h / 83 °C
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 18 h / 83 °C
  • 34
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-7-(trifluoromethyl)-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiazol-2-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
  • 35
  • [ 1187836-86-7 ]
  • (S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-7-(trifluoromethyl)-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiazol-2-yl)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere
  • 36
  • [ 1187836-86-7 ]
  • (S)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-3-(5-methyl-4-(((S)-4-methyl-1,1-dioxido-7-(trifluoromethyl)-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)thiazol-2-yl)-N-(pyridin-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 24 h / 83 °C
Multi-step reaction with 9 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere 9.1: iron(III)-acetylacetonate / isopropyl alcohol / 24 h / 83 °C
  • 37
  • [ 1187836-86-7 ]
  • benzyl (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-8-(trifluoromethyl)-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C
  • 38
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-8-(trifluoromethyl)-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethyl-N-(pyridin-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: iron(III)-acetylacetonate / isopropyl alcohol / 18 h / 83 °C
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: iron(III)-acetylacetonate / isopropyl alcohol / 18 h / 83 °C
  • 39
  • [ 1187836-86-7 ]
  • (S)-3-(4-(((S)-4-ethyl-1,1-dioxido-8-(trifluoromethyl)-4,5-dihydrobenzo[f][1,2]thiazepin-2(3H)-yl)methyl)-5-methylthiazol-2-yl)-3-(1-ethyl-4-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-2,2-dimethylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1.58 h / 100 °C / Microwave irradiation 4.2: 1.5 h / 20 °C 5.1: Chiralpak AY / isopropyl alcohol / 30 °C / 75007.5 Torr 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 2.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 0 °C 3.2: 1.5 h / 20 °C 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 25 h / 65 °C 4.2: 1 h 5.1: Chiralpak IA / ethanol / 75007.5 Torr / Resolution of racemate; Supercritical conditions 6.1: ammonium cerium (IV) nitrate / acetonitrile / 6 h / 20 °C 7.1: 1,1'-(Azodicarbonyl)dipiperidin; tributylphosphine / tetrahydrofuran / 18 h / 20 °C 8.1: hydrogen; 5%-palladium/activated carbon / methanol / 22.5 h / Inert atmosphere
  • 40
  • [ 63257-03-4 ]
  • [ 1187836-86-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tert.-butylnitrite; sodium bromide; copper(I) bromide / acetonitrile / 80 °C 2: methanol; lithium borohydride / tetrahydrofuran / 5 - 20 °C
  • 41
  • [ 1187836-86-7 ]
  • [ 1187835-49-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; sulfurous dibromide / dichloromethane / 5 - 20 °C 2: caesium carbonate; potassium iodide / acetonitrile / 24 h / 20 °C
  • 42
  • [ 1187836-86-7 ]
  • [ 1187835-56-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine; sulfurous dibromide / dichloromethane / 5 - 20 °C 2: caesium carbonate; potassium iodide / acetonitrile / 24 h / 20 °C 3: triethylamine / copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 20 h / 20 °C
  • 43
  • [ 56355-62-5 ]
  • [ 1187836-86-7 ]
YieldReaction ConditionsOperation in experiment
37.5% With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 1h; 2.1 (2-Bromo-5-methylthiazol-4-yl)methanol 2b Dissolve 2-bromo-5-methylthiazole-4-carboxylic acid ethyl ester 2a (1.25g, 4.99mmol, Shaoyuan Technology (Shanghai) Co., Ltd.) in 10mL tetrahydrofuran, stir the reaction solution to clarify, and cool to -78 , Add diisobutylaluminum hydride (1.5M, 9.95mmol) dropwise, continue the reaction for 1 hour, slowly add 1M hydrochloric acid (70mL) dropwise, add 60mL water and stir, add ethyl acetate (60mL×2) for extraction, combine the organic Phase, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and the residue obtained was purified by silica gel column chromatography with eluent system B to obtain the title compound 2b (390 mg, yield: 37.5%).
  • 44
  • [ 1187836-86-7 ]
  • 2-bromo-4-(chloromethyl)-5-methylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In dichloromethane at 0℃; for 1h; 2.2 2-Bromo-4-(chloromethyl)-5-methylthiazole 2c The compound 2b (212 mg, 1.01 mmol) was dissolved in 5 ml dichloromethane, stirred, 0 °C mL of thionyl chloride (363 mg, 3.05 mmol) was added thereto, the reaction 1 hour was continued, and the reaction solution was concentrated under reduced pressure to give the title compound 2c (230 mg) as a crude product.
  • 45
  • [ 1187836-86-7 ]
  • 6-(4-((2-bromo-5-methylthiazol-4-yl)methoxy)-6-methoxybenzofuran-2-yl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 1 h / 0 °C 2: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere
  • 46
  • [ 1187836-86-7 ]
  • 4-(4-(((6-methoxy-2-(2-methylimidazole[2,1-b][1,3,4]thiadiazol-6-yl)benzofuran-4-yl)oxy)methyl)-5-methylthiazol-2-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 1 h / 0 °C 2: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere
  • 47
  • [ 1187836-86-7 ]
  • cyclopropyl(4-(4-(4-(((6-methoxy-2-(2-methylimidazo[2,1-b][1,3,4]thiadiazole-6-yl)benzofuran-4-yl)oxy)methyl)-5-methylthiazol-2-yl)benzyl)piperazin-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 1 h / 0 °C 2: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere 4: sodium tris(acetoxy)borohydride / dichloromethane / 18 h / Inert atmosphere
  • 48
  • [ 1187836-86-7 ]
  • ((4-(4-(((6-methoxy-2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-benzofuran-4-yl)oxy)methyl)-5-methylthiazol-2-yl)phenyl)methyl)-N,N-dimethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 1 h / 0 °C 2: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere 4: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / Inert atmosphere; Cooling with ice
  • 49
  • [ 1187836-86-7 ]
  • 1-(4-(4-(4-(((6-methoxy-2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzofuran-4-yl)oxy)methyl)-5-methylthiazol-2-yl)benzyl)piperazin-1-yl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 1 h / 0 °C 2: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere 4: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / Inert atmosphere
  • 50
  • [ 1187836-86-7 ]
  • (R)-(4-(4-(4-(((6-methoxy-2-(2-methylimidazo[2,1-b][1,3,4]thiadiazole-6-yl)benzofuran-4-yl)oxy)methyl)-5-methylthiazol-2-yl)benzyl)morpholin-3-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 1 h / 0 °C 2: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere 4: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / Inert atmosphere
Same Skeleton Products
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