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[ CAS No. 1041053-44-4 ] {[proInfo.proName]}

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Chemical Structure| 1041053-44-4
Chemical Structure| 1041053-44-4
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Product Details of [ 1041053-44-4 ]

CAS No. :1041053-44-4 MDL No. :MFCD06738929
Formula : C4H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :YMJMSYXLHSSGTP-UHFFFAOYSA-N
M.W : 134.56 Pubchem ID :46912060
Synonyms :

Calculated chemistry of [ 1041053-44-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.14
TPSA : 52.05 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) : -7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.03
Log Po/w (WLOGP) : 0.78
Log Po/w (MLOGP) : -0.94
Log Po/w (SILICOS-IT) : 0.53
Consensus Log Po/w : 0.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.09
Solubility : 10.9 mg/ml ; 0.0813 mol/l
Class : Very soluble
Log S (Ali) : -0.68
Solubility : 28.4 mg/ml ; 0.211 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.2
Solubility : 8.45 mg/ml ; 0.0628 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 1041053-44-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1041053-44-4 ]

* 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 [ 1041053-44-4 ]

[ 1041053-44-4 ] Synthesis Path-Downstream   1~9

  • 1
  • 6'-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-4-methoxy-biphenyl-2,3'-dicarboxylic acid 2-benzyl ester [ No CAS ]
  • [ 1041053-44-4 ]
  • 2'-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-4-methoxy-5'-[(oxazol-2-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In DMF (N,N-dimethyl-formamide); at 20℃; for 72.0h; Part A. 2'-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-4-methoxy-5'-[(oxazol-2-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid A mixture of the compound of Example 15, Part F (75 mg, 0.138 mmol), <strong>[1041053-44-4]oxazol-2-yl-methylamine hydrochloride</strong> (28 mg, 0.208 mmol) NMM (0.012 mL, 1.10 mmol) and BOP reagent (76 mg, 0.172 mmol) in DMF (1 muL) was stirred at rt over 3 days. Reaction was worked up and product isolated as described for Example 15, Part G to provide the amide (78.3 mg, 91%). LC/MS m/z 625.3 (M+H)+.
  • 2
  • [ 848144-43-4 ]
  • [ 1041053-44-4 ]
  • [ 76-05-1 ]
  • [ 1041053-42-2 ]
YieldReaction ConditionsOperation in experiment
17% To a solution of 5-tert-butyl-2-methoxybenzoic acid (253 mg, 1 rnmol, prepared as in WO2005023761 ) in DCM/DMF (5 ml, 1 : 1 ), <strong>[1041053-44-4]oxazol-2-ylmethanamine hydrochloride</strong> (135 mg, 1 mmol), PyBOP (1.04 g, 2 mmol) and DIEA (0.87 ml, 5 mmol) were added. The resulting mixture was stirred at r.t. overnight. The DCM was evaporated and the resulting DMF solution was subjected to RP-HPLC (gradient: 40 to 99% AcN in H2O) to give the TFA-salt of the title compound (78 mg, 17%) as a yellow solid. (Calculated mass: 333.3, observed mass: 334.1 ).
  • 3
  • [ 1041053-44-4 ]
  • [ 105-36-2 ]
  • C8H12N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of <strong>[1041053-44-4]oxazol-2-ylmethanamine hydrochloride</strong> (83 mg, 0.60 mmol) in methanol (2 mL) and a 25% by weight sodium methoxide/methanol solution (0.137 mL) were added, followed by stirring at room temperature for 15 minutes. Then, insoluble matters were filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was diluted with acetonitrile (4 mL), and potassium carbonate (83 mg, 0.60 mmol) was added thereto, followed by cooling to -10 C. to -15 C. Then, ethyl 2-bromoacetate (0.066 mL, 0.60 mmol) diluted with acetonitrile (1 mL) was added dropwise. The temperature was gradually raised to room temperature, and the mixture was stirred overnight. After insoluble matters were separated by filtration, the filtrate was concentrated under reduced pressure.
  • 4
  • [ 1041053-44-4 ]
  • [ 927-68-4 ]
  • 2-(oxazol-2-yl-methylamino)ethyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at -15 - 20℃; Oxazol-2-yl methane amine hydrochloride (69mg, 0.50mmol) in acetonitrile (3mL) solution of potassium carbonate (173mg, 1.25mmol) was cooled to -10 ~ -15 was added, and acetonitrile ( diluted with 1 mL) 2-bromoethyl acetate (0.055 mL, was added dropwise 0.50 mmol), it was slowly stirred overnight raised to room temperature. After filtering off the insoluble materials, by distilling off the solvent under reduced pressure to give the title compound without purification.
  • 5
  • [ 1041053-44-4 ]
  • 2-chloro-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile [ No CAS ]
  • 4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)-2-((oxazol-2-ylmethyl)amino)quinazoline-8-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dimethyl sulfoxide; at 100℃; for 66.0h; N,N-Diisopropylethylamine (0.26 mL, 1.505 mmol) was added to 2-chloro-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile 4 (114.6 mg, 0.301 mmol) in 1,4-dioxane (1.4 mL)and dimethyl sulfoxide (1.4 mL) at room temperature, followed by<strong>[1041053-44-4]oxazol-2-ylmethanamine hydrochloride</strong> 5g (61 mg, 0.452 mmol)and the solution was heated to 100 C and stirred for sixty-six hours. The reaction mixture was poured into ether, washed withwater, dried over magnesium sulfate, filtered, and concentrated.The residue was purified by silica gel chromatography, eluting withethyl acetate:hexanes (1:1) to give 4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)-2-((oxazol-2-ylmethyl)amino)quinazoline-8-carbonitrile6g (64.8 mg, 0.111 mmol, 37.0% yield). 1H NMR (400 MHz,CD3SOCD3) d 8.45-8.26 (m, 2H), 8.04-7.84 (m, 2H), 7.72-7.52 (m,4H), 7.16-7.02 (m, 2H), 4.80-4.68 (m, 2H), 4.68-4.54 (m, 2H);LC-MS (LC-ES) M+H = 443.
  • 6
  • [ 1041053-44-4 ]
  • [ 157665-52-6 ]
  • te rt-Butyl 4-nitro-3-[(1,3-oxazol-2-ylmethyl)amino]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2.0h; To a suspension of the oxazol-2-ylmethanamine HC1 salt (491 mg, 3.65 mmol) and Intermediate 29 (800 mg, 3.32 mmol) in DMF (5 mE) was added K2C03 (1.04 g, 6.63 mmol). The reaction was stirred at 60 C. for 2 h. Additional oxazol-2-ylmethanamine HC1 salt (100 mg, 1.0 mmol) was added and reaction stirred for an additional 30 mm at 60 C. The reaction was cooled to RT then diluted with water (30 mE) and extracted with EtOAc (60 mE). The organic layer was washed with water, then brine, dried over Na2504, filtered and concentrated under reduced pressure. The orange residue was purified by flash chromatography (12 g silica gel, 0-50% EtOAc/heptane gradient) to deliver teflbutyl 4-nitro-3-((oxazol-2-ylmethyl)amino)benzoate (764 mg, 75%) as an orange solid. ?H NMR (CDC13) oe 8.48 (br s, 1H), 8.23 (d, 1H), 7.68 (d, 1H), 7.61 (d, 1H), 7.28 (dd, 1H), 7.15 (s, 1H), 4.72 (d, 2H), 1.60 (s, 9H).
75% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2.5h; To a suspension of 1 -(1 ,3-oxazol-2-yl)methanamine, hydrochloride salt (491 mg, 3.65 mmol) and fe/f-butyl 3-fluoro-4-nitrobenzoate (800 mg, 3.32 mmol) in A/,A/-dimethylformamide (5 mL) was added potassium carbonate (1 .04 g, 6.63 mmol). The reaction was stirred at 60 C for 2 hours. Additional 1 -(1 ,3-oxazol-2-yl)methanamine, hydrochloride salt (100 mg, 1 .0 mmol) was added and the reaction was stirred for an additional 30 minutes at 60 C. The reaction was cooled to room temperature then diluted with water (30 mL) and extracted with EtOAc (60 mL). The organic layer was washed with water, then saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The orange residue was purified by flash chromatography (12 g silica gel, 0-50% EtOAc / heptane gradient) to deliver P25 (764 mg, 75%) as an orange solid. NMR (CDCI3) d 8.48 (br s, 1 H), 8.23 (d, 1 H), 7.68 (d, 1 H), 7.61 (d, 1 H), 7.28 (dd, 1 H), 7.15 (s, 1 H), 4.72 (d, 2H), 1 .60 (s, 9H).
  • 7
  • [ 1041053-44-4 ]
  • methyl 6-chloro-5-nitropyridine-2-carboxylate [ No CAS ]
  • methyl 6-[(1,3-oxazol-2-ylmethyl)amino]-5-nitropyridine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 25℃; for 14.0h; Triethylamine (532 mg, 5.26 mmol) was added to a suspension of 1-(1,3-oxazol-2-yl)methanamine, hydrochloride salt (236 mg, 1.75 mmol) and methyl 6-chloro-5-nitropyridine-2-carboxylate (386 mg, 1.78 mmol) in tetrahydrofuran (5 mL). After the reaction mixture had been stirred at 25 C. for 14 hours, it was poured into water (30 mL) and extracted with dichloromethane (2×50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo; silica gel chromatography (Gradient: 0% to 5% methanol in dichloromethane) afforded C65 as a yellow solid. Yield: 310 mg, 1.11 mmol, 63%. LCMS m/z 278.7 [M+H]+. 1H NMR (400 MHz, chloroform-d) delta 8.69-8.61 (br m, 1H), 8.58 (d, J=8.4 Hz, 1H), 7.65 (d, J=0.8 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.11 (d, J=1.0 Hz, 1H), 5.07 (d, J=5.3 Hz, 2H), 3.97 (s, 3H).
  • 8
  • [ 1041053-44-4 ]
  • C13H11N5O3 [ No CAS ]
  • C17H15N7O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
22.25% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 8h; 49; 61 EXAMPLE 49: SYNTHESIS OF COMPOUND 196 To a mixture of compound 1 (100 mg, 350.56 umol, 1 eq) and compound 2 (56.61 mg, 420.67 umol, 1.2 eq, HCl) in DMF (2 mL) was added DIEA (135.92 mg, 1.05 mmol, 183.18 uL, 3 eq) and HATU (199.94 mg, 525.84 umol, 1.5 eq), the mixture was stirred at 20 °C for 8 hr. LCMS showed desired MS was detected. The reaction mixture was diluted with water (5 mL), extracted with EtOAc (5 mL*2), dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC (column: Boston Green ODS 150*30mm*5um;mobile phase: [water(0.225%FA)-ACN];B%: 10%-40%,10min) to give compound 196 (30 mg, 78.01 umol, 22.25% yield, 95% purity) as yellow solid. 1H NMR (400MHz, DMSO-d6) d = 12.42 (br. s, 1H), 9.52 (t, J = 5.9 Hz, 1H), 8.38 (s, 1H), 8.07 (d, J = 0.8 Hz, 1H), 7.47 - 7.43 (m, 1H), 7.18 (d, J = 0.8 Hz, 1H), 6.83 (br. d, J = 1.9 Hz, 1H), 5.05 (s, 2H), 4.58 (d, J = 6.0 Hz, 2H), 4.28 (br. t, J = 5.6 Hz, 2H), 3.12 (br. t, J = 5.1 Hz, 2H) 13C NMR (101MHz, DMSO-d6) d = 169.09, 160.95, 159.61, 154.38, 140.31, 127.53, 124.09, 111.48, 102.75, 102.64, 43.35, 42.86, 36.58, 23.63. LCMS: Rt=0.700 min, [M+H]+= 366.2
  • 9
  • [ 1041053-44-4 ]
  • [ 69651-48-5 ]
  • tert-butyl (S)-(1-(4-hydroxyphenyl)-2-((oxazol-2-ylmethyl)amino)-2-oxoethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 5℃; for 0.166667h; Stage #2: 1-(1,3-oxazol-2-yl)methanamine hydrochloride salt In N,N-dimethyl-formamide at 5 - 20℃; for 2h; Step 1: tert-butyl (S)-(1-(4-hydroxyphenyl)-2-((oxazol-2-ylmethyl)amino)-2-oxoethyl)carbamate (163d). The title compound (417 mg, 64%) was synthesized from (S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetic acid 162 (500 mg, 1.87 mmol) and 2-aminomethyl-oxazole hydrochloride (277 mg, 2.06 mmol) according to the same procedure described in step 1 in the preparation of intermediate 163a in the synthesis of compound 92 without further purification. LCMS (ES+) m/z calculated for C17H21N3O5 347.15, found 292 (M+H-tBu)+.
64% Stage #1: N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 5℃; for 0.166667h; Stage #2: 1-(1,3-oxazol-2-yl)methanamine hydrochloride salt In N,N-dimethyl-formamide at 5 - 20℃; for 2h; Step 1: tert-butyl (S)-(1-(4-hydroxyphenyl)-2-((oxazol-2-ylmethyl)amino)-2-oxoethyl)carbamate (163d). The title compound (417 mg, 64%) was synthesized from (S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetic acid 162 (500 mg, 1.87 mmol) and 2-aminomethyl-oxazole hydrochloride (277 mg, 2.06 mmol) according to the same procedure described in step 1 in the preparation of intermediate 163a in the synthesis of compound 92 without further purification. LCMS (ES+) m/z calculated for C17H21N3O5 347.15, found 292 (M+H-tBu)+.
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