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[ CAS No. 177908-37-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 177908-37-1
Chemical Structure| 177908-37-1
Chemical Structure| 177908-37-1
Structure of 177908-37-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 177908-37-1 ]

CAS No. :177908-37-1 MDL No. :MFCD18632623
Formula : C7H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :KUKASNZJTIKRMH-UHFFFAOYSA-N
M.W :129.20 Pubchem ID :18331273
Synonyms :

Calculated chemistry of [ 177908-37-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 37.56
TPSA : 46.25 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) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 0.12
Log Po/w (WLOGP) : 0.64
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 0.77
Consensus Log Po/w : 0.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.72
Solubility : 24.8 mg/ml ; 0.192 mol/l
Class : Very soluble
Log S (Ali) : -0.65
Solubility : 29.1 mg/ml ; 0.225 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.72
Solubility : 24.6 mg/ml ; 0.191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 177908-37-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 UN#:3259
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 177908-37-1 ]

* 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 [ 177908-37-1 ]

[ 177908-37-1 ] Synthesis Path-Downstream   1~72

YieldReaction ConditionsOperation in experiment
(1) trans-4-amino-1-methylcyclohexanol Melting point: 225-230 C. Rf value: 0.13 (aluminium oxide; petroleum ether/ethyl acetate =10:4)
  • 2
  • [ 177908-37-1 ]
  • 4-(3,5-dichloropyridin-2-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
  • 3
  • [ 177908-37-1 ]
  • 4-(3,5-difluoropyridin-2-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
  • 4
  • [ 177908-37-1 ]
  • 4’-chloro-2’-cyano-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)biphenyl-4-sulfonamide [ No CAS ]
  • 5
  • [ 177908-37-1 ]
  • 4’-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-2’-(trifluoromethyl)biphenyl-4-sulfonamide [ No CAS ]
  • 6
  • [ 177908-37-1 ]
  • 2’4’,6’-trifluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)biphenyl-4-sulfonamide [ No CAS ]
  • 7
  • [ 177908-37-1 ]
  • 3-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide [ No CAS ]
  • 8
  • [ 177908-37-1 ]
  • 4-(3,5-difluoropyridin-2-yl)-3-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
  • 9
  • [ 177908-37-1 ]
  • 4-(3,5-dichloropyridin-2-yl)-3-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
  • 10
  • [ 177908-37-1 ]
  • 2,2’,4’-trifluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-[1,1‘-biphenyl]-4-sulfonamide [ No CAS ]
  • 11
  • [ 177908-37-1 ]
  • 2’-cyano-4’-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-[1,1‘-biphenyl]-4-sulfonamide [ No CAS ]
  • 12
  • [ 177908-37-1 ]
  • 4’-cyano-2’-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-[1,1‘-biphenyl]-4-sulfonamide [ No CAS ]
  • 13
  • [ 177908-37-1 ]
  • N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide [ No CAS ]
  • 14
  • [ 177908-37-1 ]
  • 4-(4-chloro-2-cyanophenyl)benzene-1-sulfonyl chloride [ No CAS ]
  • 4’-chloro-2’-cyano-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)biphenyl-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 5 - 25℃; for 40h; To a 10 L flask was charged finely divided (lr,4r)-4-amino-1-methylcyclohexan-1-ol (123.7 g, 0.957 mol) and dichloromethane (2400 mL). Triethylamine (534 mL, 3.830 mol) was added dropwise. The suspension cooled to below 5C and 4-(4-chloro-2- cyanophenyl)benzene-1-sulfonyl chloride (298.9 g, 0.957 mol) in dichloromethane(768 mL) added dropwise maintaining the temperature at less than 25C. The reaction mixture was allowed to warm to room temperature and stirred for 40 hours. The reaction mixture was cooled to below 1000 and 2 M aqueous hydrochloric acid (2090 mL) added dropwise while maintaining the temperature at less than 25C (exothermic addition and white fumes observed). The phases were separated and the organic layer was washedwith water (2090 mL). The organics were dried over anhydrous magnesium sulphate, filtered, and the residue was washed with dichloromethane (2 x 50 mL). The combined filtrates were then combined with the crude product from a similar smaller scale reaction of 4-(4-chloro-2-cyanophenyl)benzene-1-sulfonyl chloride (50 g) and (1 r,4r)-4-amino-1- methylcyclohexan-1-ol, and all of the combined materials adsorbed directly onto silica(800 g). This was purified by chromatography on silica (8000 g) eluting initially with ethyl acetate: dichloromethane 20:80, and then sequentially with mixtures of ethyl acetate:dichloromethane 30:70, 40:60, 50:50, followed by neat ethyl acetate. Fractions containing the product were combined and concentrated to afford a yellow solid. This material was dried in a vacuum oven overnight at 40C to afford the title compound(406.8 g; overall 88 % yield). Analysis by NMR indicated a purity of >97 %.1H NMR: (270 MHz; CDCI3) O 8.02 (d, J = 8.6 Hz, 2H), 7.78 (d, J = 2 Hz, 1H), 7.73-7.63(m, 3H), 7.49 (d, J = 8.5 Hz, 1H), 4.89 (d, J = 7Hz, 1H), 3.38 (m, 1H), 1.98-1.75 (m, 2H),1.75-1.3 (m, 7H, m), 1.23 (5, 3H).HPLC: mobile phase A: purified water + 0.1% trifluoroacetic acid, mobile phase B:acetonitrile + 0.1% trifluoroacetic acid; Column: Fortis C18 4.6 x 150mm; 3 uM; Flow rate:1.0 mLlmin. Run time: 30 mins - starting solvent 5:95 B:A is increased linearly to 95:5B:A over the first 15 mins, held at 95:5 B:A for the final 15 mm. Retention time 12.0 mm.Mass Spectrum: Bruker Esquire 3000 Plus Ion Trap MS; Positive ion polarity, ESI: m/z403 (M-H)+.
  • 15
  • 4-bromo-3-fluorobenzene-1-sulfonyl chloride [ No CAS ]
  • [ 177908-37-1 ]
  • 4-bromo-3-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 4h; Diisopropylethylamine (20 mL, 116.2 mmol) was added to a solution of (1 r,4r)-4-amino-1- methylcyclohexanol (3 g, 23.2 mmol) in dichloromethane (150 mL) and the reaction mixture was cooled to 0C. 4-Bromo-3-fluorobenzene-1-sulfonyl chloride (6.98 g,25.5 mmol) was added as solid and the reaction mixture was allowed to stir at room temperature for 4 hours. The reaction mixture was neutralized with 1 M hydrochloric acid and the compound was extracted into dichloromethane. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue obtained was washed with n-pentane, filtered and dried to give the title compound(7 g, 82%). MS (ESI) m/z 368 (M+H)).
82% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 4h; Synthesis C 4-Bromo-3-fluoro-/V-((1 r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide Diisopropylethylamine (20 ml_, 1 16.2 mmol) was added to a solution of (1 r,4r)-4-amino-1- methylcyclohexanol (3 g, 23.2 mmol) in dichloromethane (150 ml.) and the reaction mixture was cooled to 0C. 4-Bromo-3-fluorobenzene-1 -sulfonyl chloride (6.98 g, 25.5 mmol) was added as solid and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was neutralized with 1 M hydrochloric acid and the compound was extracted into dichloromethane. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue obtained was washed with n-pentane, filtered and dried to give the title compound (7 g, 82%). MS (ESI) m/z 368[M+H].
  • 16
  • [ 177908-37-1 ]
  • [ 98-58-8 ]
  • 4-bromo-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 4h; Diisopropylethylamine (24 mL, 137.8 mmol) was added to a solution of (1 r,4r)-4-amino-1- methylcyclohexanol (3.6 g, 27.86 mmol) in dichloromethane (150 mL) and the reactionmixture was cooled to 0O. 4-Bromobenzene-1-sulfonyl chloride (7.83 g, 30.6 mmol) was added as solid and the reaction mixture was allowed to stir at room temperature forhours. The reaction mixture was neutralized with 1 M hydrochloric acid and the compound was extracted into dichloromethane. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue obtainedwas washed with pentane, filtered and dried to give the title compound (7 g, 72%).1H NMR: (400 MHz; ODd3) O 7.74 (2H, d), 7.65 (2H, d), 4.77-4.61 (1H, m), 3.33-3.23 (1H, m), 1.85-1.75 (2H, m), 1.63-1.51 (2H, m), 1.49-1.30 (4H, m), 1.20 (3H, 5).LCMS: (Run time: 3.5 mm): Retention time: 1.33 mm (97%, MS (ESI) m/z346 (M-H)).
72% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 4h; Synthesis E 4-Bromo-/V-((1 r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide Diisopropylethylamine (24 mL, 137.8 mmol) was added to a solution of (1 r,4r)-4-amino-1- methylcyclohexanol (3.6 g, 27.86 mmol) in dichloromethane (150 mL) and the reaction mixture was cooled to 0C. 4-Bromobenzene-1-sulfonyl chloride (7.83 g, 30.6 mmol) was added as solid and the reaction mixture was allowed to stir at room temperature for 4 hours. The reaction mixture was neutralized with 1 M hydrochloric acid and the compound was extracted into dichloromethane. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue obtained was washed with pentane, filtered and dried to give the title compound (7 g, 72%). 1H NMR (400 MHz; CDCI3) δ: 7.74 (2H, d), 7.65 (2H, d), 4.77 - 4.61 (1 H, m), 3.33 - 3.23 (1 H, m), 1 .85-1.75 (2H, m), 1.63-1 .51 (2H, m), 1 .49-1.30 (4H, m), 1 .20 (3H, s). LCMS: (Run time: 3.5 min): Retention time: 1.33 min (97%, MS (ESI) m/z 346[M-H].
  • 17
  • (1r,4r)-4-(dibenzylamino)-1-methylcyclohexan-1-ol [ No CAS ]
  • [ 177908-37-1 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen; palladium(II) hydroxide; In methanol; water; at 80℃; under 38002.6 Torr;Autoclave; Palladium hydroxide (50% wet with water; 2.0 g) was added to a stirred solution of(lr,4r)-4-(dibenzylamino)-1-methylcyclohexanol (7.5 g, 24.2 mmol) in methanol (100 mL) in a 300 mL autoclave. The autoclave was charged with hydrogen (50 atm; -5 MPa) and heated at 80C for 24 hours. The mixture was cooled and the catalyst filtered off. The filtrate was returned to the autoclave and palladium hydroxide (50% wet with water; 3.0 g)was added. The autoclave was charged with hydrogen (50 atm; -50 MPa) and heated at80C overnight. The mixture was cooled and filtered through celite and the filtrate was concentrated to give the title compound as an off-white gummy solid (3.2 g, quant.). 1H NMR: (400 MHz; ODd3) O 2.86-2.76 (1H, m), 1.84-1.76 (2H, m), 1.75-1.63 (2H, m),1.55-1.43 (2H, m), 1.30-1.17 (5H, m).
100% With hydrogen; palladium(II) hydroxide; In methanol; water; at 80℃; under 38002.6 Torr;Autoclave; Synthesis A (1 r,4r)-4-Amino-1 -methylcyclohexan-1 -ol Palladium hydroxide (50% wet with water; 2.0 g) was added to a stirred solution of (1 r,4r)-4-(dibenzylamino)-1 -methylcyclohexanol (7.5 g, 24.2 mmol) in methanol (100 mL) in a 300 mL autoclave. The autoclave was charged with hydrogen (50 atm; ~5 MPa) and heated at 80C for 24 hours. The mixture was cooled and the catalyst filtered off. The filtrate was returned to the autoclave and palladium hydroxide (50% wet with water; 3.0 g) was added. The autoclave was charged with hydrogen (50 atm; -50 MPa) and heated at 80C overnight. The mixture was cooled and filtered through celite and the filtrate was concentrated to give the title compound as an off-white gummy solid (3.2 g, quant.). 1H NMR (400 MHz; CDCI3) δ: 2.86 - 2.76 (1 H, m), 1 .84 - 1.76 (2H, m), 1.75 - 1 .63 (2H, m), 1.55 - 1.43 (2H, m), 1 .30 - 1.17 (5H, m).
  • 18
  • [ 177908-37-1 ]
  • 2-(methylsulfonyl)-4-(1-(tetrahydro-2H-pyran-2-yl)-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-4-yl)pyrimidine [ No CAS ]
  • C23H30F3N5O2 [ No CAS ]
  • 19
  • [ 177908-37-1 ]
  • 2-(methylsulfonyl)-4-(1-(tetrahydro-2H-pyran-2-yl)-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-4-yl)pyrimidine [ No CAS ]
  • C18H22F3N5O [ No CAS ]
  • 20
  • [ 177908-37-1 ]
  • 3-chloro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide [ No CAS ]
  • 21
  • [ 177908-37-1 ]
  • 4'-chloro-2'-cyano-2-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]
  • 22
  • [ 177908-37-1 ]
  • 2'-chloro-4'-cyano-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]
  • 23
  • [ 177908-37-1 ]
  • 2,4'-dichloro-2'-cyano-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]
  • 24
  • [ 177908-37-1 ]
  • 4'-cyano-2-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]
  • 25
  • [ 177908-37-1 ]
  • 4-(5-chloro-3-cyanopyridin-2-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
  • 26
  • [ 177908-37-1 ]
  • [ 874801-46-4 ]
  • 4-bromo-3-chloro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; Synthesis G 4-Bromo-3-chloro-/V-((1 r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamid To a solution of (1 r,4r)-4-amino-1 -methylcyclohexanol (1.2 g, 9.29 mmol) in dichloromethane (50 mL) was added diisopropylethylamine (2.99 g, 23.13 mmol) and the reaction mixture was cooled to 0C. 4-Bromo-3-chlorobenzenesulfonyl chloride (2.61 g, 9.0 mmol) was added and the reaction mixture was allowed to stir at room temperature for 3-4 hours. The reaction mixture was neutralized with 1 M hydrochloric acid and the compound was extracted into dichloromethane. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The residue obtained was washed with pentane, filtered and dried to afford the title compound (2.1 g, 59%). MS (ESI) m/z 380[M-H].
  • 27
  • [ 177908-37-1 ]
  • 3-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)benzoic acid [ No CAS ]
  • N-(2-chloro-6-methylphenyl)-2-((3-(((1R,4R)-4-hydroxy-4-methylcyclohexyl)carbamoyl)phenyl)amino)thiazole-5-carboxamide [ No CAS ]
  • 28
  • [ 177908-37-1 ]
  • [ 32315-10-9 ]
  • 4-(azetidin-3-yloxy)benzo[d]thiazole hydrochloride [ No CAS ]
  • 3-(benzo[d]thiazol-4-yloxy)-N-((trans)-4-hydroxy-4-methylcyclohexyl)azetidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% To a stirred solution of triphosgene (20 mg, 0.07 mmol) in DCM (1 mL) was added a mixture of frans-4-amino-1 -methylcyclohexanol (Intermediate 57) (30 mg, 0.23 mmol) and N,N- diisopropylethylamine (0.05 mL, 0.3 mmol) in DCM (2 mL) dropwise over 5 minutes. The mixture was stirred an additional 10 minutes, and then a mixture of 4-(azetidin-3- yloxy)benzo[d]thiazole hydrochloride (Intermediate 28) (50 mg, 0.21 mmol) and N,N- diisopropylethylamine (0.08 mL, 0.5 mmol) in DCM (1 mL) was added in one portion. After 18 h, the reaction was partitioned between DCM and 0.5 N aqueous HCI. The aqueous layer was further extracted with DCM and the combined organic layers were washed with saturated NaHCC>3 and brine, dried over Na2SC>4, concentrated and purified by silica gel chromatography, eluting with a 10%-100% EtOAc:EtOH (3:1) in hexanes gradient, to give the title compound as a white solid (28 mg, 38%). 1H NMR (400 MHz, CD3SOCD3) δ 1 .08 (s, 3 H), 1 .20-1 .39 (m, 4 H), 1 .44-1 .52 (m, 2 H), 1 .59-1 .67 (m, 2 H), 3.32-3.40 (m, 1 H), 3.78-3.84 (m, 2 H), 4.19 (s, 1 H), 4.25-4.30 (m, 2 H), 5.16-5.22 (m, 1 H), 6.10 (d, J = 8 Hz, 1 H), 6.82 (d, J = 8 Hz, 1 H), 7.38 (t, J = 8 Hz, 1 H), 7.72 (d, J = 8 Hz, 1 H), 9.27 (s, 1 H); LC-MS (LC-ES) M+H = 362.
  • 29
  • [ 1236405-13-2 ]
  • [ 177908-37-1 ]
YieldReaction ConditionsOperation in experiment
100% With palladium on activated charcoal; hydrogen; In methanol; for 1h; Palladium on carbon (217 mg, 0.20 mmol) was added to benzyl (frans-4-hydroxy-4- methylcyclohexyl)carbamate (Intermediate 57A) (524 mg, 1 .99 mmol) under a nitrogen atmosphere with enough methanol to wet the catalyst. The reaction vessel was fitted with a hydrogen balloon, and the vessel was repeatedly evacuated and purged with hydrogen, then stirred for 1 h under a hydrogen atmosphere. The vessel was repeatedly evacuated and purged with nitrogen, filtered through Celite, and concentrated to give the title compound (257 mg, quantitative) as a white solid. 1H NMR (400 MHz, CD3SOCD3) δ 1 .08 (s, 3 H), 1 .09-1 .19 (m, 2 H), 1 .26-1 .38 (m, 2 H), 1 .45-1 .56 (m, 2 H), 1 .59-1 .72 (m, 2 H), 2.59-2.66 (m, 1 H).
  • 30
  • [ 177908-37-1 ]
  • (trans)-3-(2-(difluoromethoxy)-5-fluorophenoxy)cyclobutanecarboxylic acid [ No CAS ]
  • (trans)-3-(2-(difluoromethoxy)-5-fluorophenoxy)-N-((trans)-4-hydroxy-4-methylcyclohexyl)cyclobutanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; for 17h; To a DMF (1 mL) solution of (irans)-3-(2-(difluoromethoxy)-5- fluorophenoxy)cyclobutanecarboxylic acid (Intermediate 4) (75 mg, 0.27 mmol), (trans)-4- amino-1 -methylcyclohexanol (39 mg, 0.30 mmol) and /V,/V-diisopropylethylamine (0.19 mL, 1 .1 mmol) was added, dropwise, a 50% solution of T3P in ethyl acetate (0.25 mL, 0.42 mmol). The mixture was stirred 17 hours, quenched with saturated aqueous sodium bicarbonate to a pH of 8-9. The reaction was extracted with ethyl acetate (2X). The combined organics were washed with water, followed by brine, then dried over sodium sulfate, filtered and concentrated under reduce pressure. The residue was purified by silica gel chromatography, eluting with a 10-50% ethyl acetate in heptanes gradient. The appropriate fractions were concentrated under reduced pressure to afford the title compound (54 mg, 51 %). 1H NMR (400 MHz, CD3OD) δ 1 .23 (s, 3 H), 1 .34-1 .46 (m, 2 H), 1 .50-1 .60 (m, 2 H), 1 .63-1 .72 (m, 2 H), 1 .80-1 .92 (m, 2 H), 2.36-2.46 (m, 2 H), 2.59-2.70 (m, 2 H), 3.06-3.18 (m, 1 H), 3.70-3.82 (m, 1 H), 4.93 (quin, J = 6 Hz, 1 H), 6.61 -6.71 (m, 2 H), 6.66 (t, J = 72 Hz, 1 H), 7.14 (dd, J = 9, 6 Hz, 1 H), 7.86 (d, J = 8 Hz, 1 H) ; LC-MS (LC-ES) M+H = 388.
  • 31
  • [ 177908-37-1 ]
  • (trans)-3-(quinolin-8-yloxy)cyclobutanecarboxylic acid [ No CAS ]
  • (trans)-N-((trans)-4-hydroxy-4-methylcyclohexyl)-3-(quinolin-8-yloxy)cyclobutanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% To a DMF (1 .5 mL) solution of (frans)-3-(quinolin-8-yloxy)cyclobutanecarboxylic acid (Intermediate 79) (35 mg, 0.14 mmol) was added HATU (66 mg, 0.17 mmol) and N,N- diisopropylethylamine (0.05 mL, 0.3 mmol). After 15 minutes, (frans)-4-amino-1 - methylcyclohexanol (Intermediate 57) (30 mg, 0.22 mmol) was added, and the mixture was stirred for 18 h and then loaded onto a semi-prep HPLC (NH4OH as modifier) to afford the title compound as a white solid (31 mg, 61 %). 1H NMR (400 MHz, CD3OD) δ 1 .24 (s, 3 H), 1 .36- 1 .7 (m, 2 H), 1 .51 -1 .61 (m, 2 H), 1 .62-1 .72 (m, 2 H), 1 .81 -1 .91 (m, 2 H), 2.55-2.65 (m, 2 H), 2.69-2.80 (m, 2 H), 3.19 (dq, J = 10, 5 Hz, 1 H), 3.78 (dt, J = 9, 5 Hz, 1 H), 5.13-5.19 (m, 1 H), 6.98 (dd, J = 7, 2 Hz, 1 H), 7.43-7.49 (m, 2 H), 7.53 (dd, J = 8, 4 Hz, 1 H), 8.29 (dd, J = 8, 2 Hz, 1 H), 8.81 (dd, J = 4, 2 Hz, 1 H); LC-MS (LC-ES) M+H = 355.
  • 32
  • [ 16801-63-1 ]
  • [ 177908-37-1 ]
  • 33
  • [ 177908-37-1 ]
  • [ 1428368-75-5 ]
  • (1r,4r)-4-((4-(3,5-dimethylisoxazol-4-yl)-2-nitrophenyl)amino)-1-methylcyclohexan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate; In acetonitrile; for 1h;Reflux; 4-(4-Fluoro-3-nitrophenyl)-3,5-dimethylisoxazole (1.618 g, 6.85 mmol), (lr,4r)-4- amino-1 -methyl cyclohexanol (1.0 g, 7.74 mmol) and potassium carbonate (1.638 g, 11.85 mmol) were heated to reflux in acetonitrile (20.75 mL) for 1 h. The reaction was cooled down to RT and stirred overnight. The mixture was diluted with water (200 mL) then the orange precipitate was collected by filtration. The crude product (ca. 4 g as a wet solid) was purified by chromatography on the Companion (24 g column, 0-50% (0390) EtOAc/DCM) to afford (lr,4r)-4-((4-(3,5-dimethylisoxazol-4-yl)-2-nitrophenyl)amino)- 1-methylcyclohexanol (2.0 g, 79%) as an orange solid; Rt 2.10 min (method 1); m/z 346 (M+H)+ (ES+).
  • 34
  • [ 177908-37-1 ]
  • [ 874801-46-4 ]
  • 4-bromo-3-chloro-N-((1R,4R)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 0 - 20℃; for 7h; A solution of (I s,3s)-3-amino-I -(trifluoromethyl)cyclobutan-I -ol hydrochloride (ActivateScientific, CAS Nr. 1408075-93-3) (249 mg, 1.30 mmol) in pyridine (6.5 ml) was treated with 4-bromo-3-methylbenzenesulfonyl chloride (Sigma-Aldrich, CAS Nr. 72256-93-0) (350 mg, 1 .30 mmol) and stirred at 50 C for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting product was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to afford the title compound. :_Intermediate 58a: 4-bromo-3-chloro-N-((1 R,4R)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide.The title compound was prepared in an analogous manner to 4-bromo-N-(3-hydroxy-3- (trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide (Intermediate 2a) using 4-bromo-3- chlorobenzene-1-sulfonyl chloride and (1 R,4R)-4-amino-1-methylcyclohexanol. The reaction mixture was stirred at 0 C for 30 mm and at RT for 6.5 h, then diluted with EtOAc. The organic layer was washed twice with a IN aq. NH4CI. The aq. layer was extracted twice with EtOAc. Thecombined organic layers were washed wih brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (0 to 40% EtOAc in Cyclohexane) to give the title compound as a white solid.(UPLC-MS) tR 0.94 mm; 380.0/382.1/384.0 [M-H].
  • 35
  • [ 177908-37-1 ]
  • 6-chloro-7-cyclopropyl-1,8-naphthyridine-3-carboxylic acid [ No CAS ]
  • 6-chloro-7-cyclopropyl-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-1,8-naphthyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; for 2.5h; (1 r,4r)-4-Amino-1 -methylcyclohexan-1 -ol (0.031 g, 0.240 mmol, Intermediate 21 ) was added 6-chloro-7-cyclopropyl-1 ,8-naphthyridine-3-carboxylic acid (0.053 g, 0.213 mmol, Intermediate 18) in N,N-dimethylformamide (2.5 ml_). Then, N,N-diisopropylethylamine (0.05 ml_, 0.287 mmol) was added, followed by 1 -[bis(dimethylamino)methylene]-1 H-1 ,2,3- triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (0.098 g, 0.258 mmol) and the reaction mixture was stirred for 2.5 hours and concentrated. Dichloromethane and methanol were added to the residue and it was purified via silica gel chromatography, eluting with (3:1 ethyl acetate:ethanol):hexanes (0:1 to 3:2) to give a material which was dissolved in ethyl acetate. Once crystals formed, the mixture was partially concentrated via a stream of nitrogen and the solids collected by filtration, air-dried, then dried under vacuum overnight to give 6-chloro-7- cyclopropyl-N-((1 r,4r)-4-hydroxy-4-methylcyclohexyl)-1 ,8-naphthyridine-3-carboxamide ethyl acetate solvate (0.058 g, 0.129 mmol, 60.7 % yield) as an off-white crystalline solid. 1H NMR (400 MHz, CD3SOCD3) δ 1 .15 (s, 3 H), 1 .20-1 .26 (m, 4 H), 1 .40-1 .54 (m, 4 H), 1 .56-1 .64 (m, 2 H), 1 .74-1 .86 (m, 2 H), 2.68-2.78 (m, 1 H), 3.80-3.92 (m, 1 H), 4.32 (s, 1 H), 8.59 (d, J = 8 Hz, 1 H), 8.69 (s, 1 H), 8.76 (d, J = 3 Hz, 1 H), 9.32 (d, J = 3 Hz, 1 H); LC-MS (LC-ES) M+H = 360.
  • 36
  • [ 1236405-14-3 ]
  • [ 177908-37-1 ]
YieldReaction ConditionsOperation in experiment
100% With palladium on activated charcoal; hydrogen; In methanol; for 1h; Palladium on carbon (217 mg, 0.20 mmol) was added to benzyl (trans-4-hydroxy-4- methylcyclohexyl)carbamate (524 mg, 1 .99 mmol) under a nitrogen atmosphere with enough methanol to wet the catalyst. The reaction vessel was fitted with a hydrogen balloon, and the vessel was repeatedly evacuated and purged with hydrogen, then stirred for 1 h under a hydrogen atmosphere. The vessel was repeatedly evacuated and purged with nitrogen, filtered through Celite, and concentrated to give the title compound (257 mg, 1 .98 mmol, 100 % yield) as a white solid. 1H NMR (400 MHz, CD3SOCD3) δ 1 .08 (s, 3 H), 1 .09-1 .19 (m, 2 H), 1 .26-1 .38 (m, 2 H), 1 .45-1 .56 (m, 2 H), 1 .59-1 .72 (m, 2 H), 2.59-2.66 (m, 1 H).
  • 37
  • [ 177908-37-1 ]
  • lithium (S)-6-chloro-7-(2-methylazetidin-1-yl)-1,8-naphthyridine-3-carboxylate [ No CAS ]
  • 6-chloro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-7-((S)-2-methylazetidin-1-yl)-1,8-naphthyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Ν,Ν-Diisopropylethylamine (0.158 mL, 0.907 mmol) was added to lithium (S)-6-chloro- 7-(2-methylazetidin-1 -yl)-1 ,8-naphthyridine-3-carboxylate (0.0643 g, 0.227 mmol, Intermediate 36) in N,N-dimethylformamide (0.76 mL) at room temperature. Then, (1 r,4r)-4-amino-1 - methylcyclohexan-1 -ol (0.044 g, 0.340 mmol, Intermediate 21 ) was added and the reaction mixture was stirred for five minutes. Then, n-propylphosphonic acid anhydride (0.270 mL, 0.453 mmol) was added and the reaction mixture was stirred for sixteen hours. The reaction mixture was concentrated. The resulting residue was purified by RP HPLC, eluting with acetonitrile:water with 0.1 % ammonium hydroxide (5:95 to 100:0), then further purified by silica gel chromatography, eluting with methanokethyl acetate (0:1 to 3:7) to give 6-chloro-N-((1 r,4S)- 4-hydroxy-4-methylcyclohexyl)-7-((S)-2-methylazetidin-1 -yl)-1 ,8-naphthyridine-3-carboxamide (0.0712 g, 0.174 mmol, 77 % yield). 1H NMR (400 MHz, CD3SOCD3) δ 1 .15 (s, 3 H), 1 .48 (d, J = 6 Hz, 3 H), 1 .38-1 .54 (m, 4 H), 1 .54-1 .62 (m, 2 H), 1 .72-1 .82 (m, 2 H), 1 .90-2.02 (m, 1 H), 2.42-2.54 (m, 1 H), 3.76-3.88 (m, 1 H), 4.24 (dt, J = 9, 7 Hz, 1 H), 4.31 (s, 1 H), 4.53 (dt, J = 9, 6 Hz, 1 H), 4.79 (h, J = 8 Hz, 1 H), 8.33 (s, 1 H), 8.39 (d, J = 8 Hz, 1 H), 8.53 (d, J = 2 Hz, 1 H), 9.13 (d, J = 2 Hz, 1 H); LC-MS (LC-ES) M+H = 389.
77% N,N-Diisopropylethylamine (0.158 mL, 0.907 mmol) was added tolithium (S)-6-chloro-7-(2-methylazetidin-1-yl)-1,8-naphthyridine-3-carboxylate 7x (0.0643 g, 0.227 mmol) in N,N-dimethylformamide(0.76 mL) at room temperature. Then, <strong>[177908-37-1](1r,4r)-4-amino-1-methylcyclohexan-1-ol</strong> 8l (0.044 g, 0.340 mmol, AstaTech) was added and thereaction mixture was stirred for five minutes. Then, n-propylphosphonicacid anhydride (0.270 mL, 0.453 mmol) was added and the reactionmixture was stirred for sixteen hours. The reaction mixture wasconcentrated. The resulting residue was purified by RP HPLC, elutingwith acetonitrile:water with 0.1% ammonium hydroxide (5:95 to100:0), then further purified by silica gel chromatography, eluting withmethanol:ethyl acetate (0:1 to 3:7) to give 6-chloro-N-((1r,4S)-4-hydroxy-4-methylcyclohexyl)-7-((S)-2-methylazetidin-1-yl)-1,8-naphthyridine-3-carboxamide 1bf (0.0712 g, 0.174 mmol, 77% yield). 1H NMR(400 MHz, CD3SOCD3) δ 1.15 (s, 3H), 1.48 (d, J = 6 Hz, 3H), 1.38-1.54(m, 4H), 1.54-1.62 (m, 2H), 1.72-1.82 (m, 2H), 1.90-2.02 (m, 1H),2.42-2.54 (m, 1H), 3.76-3.88 (m, 1H), 4.24 (dt, J = 9, 7 Hz, 1H), 4.31 (s,1H), 4.53 (dt, J = 9, 6 Hz, 1H), 4.79 (h, J = 8 Hz, 1H), 8.33 (s, 1H), 8.39(d, J = 8 Hz, 1H), 8.53 (d, J = 2 Hz, 1H), 9.13 (d, J = 2 Hz, 1H); LC-MS(LC-ES) C20H25ClN4O2 M + H = 389; tR = 0.60 min, 100% purity.
  • 38
  • [ 177908-37-1 ]
  • 7-cyclopropyl-1,6-naphthyridine-3-carboxylic acid [ No CAS ]
  • 7-cyclopropyl-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-1,6-naphthyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.9% N,N-Diisopropylethylamine (0.092 mL, 0.525 mmol) was added to a stirred solution of 7-cyclopropyl-1 ,6-naphthyridine-3-carboxylic acid (75 mg, 0.350 mmol, Intermediate 1) in N,N- dimethylformamide (1 .5 mL) at room temperature. Then, 1 -[bis(dimethylamino)methylene]-1 H- 1 ,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (200 mg, 0.525 mmol) was added. After stirring for 15 minutes, (1 r,4r)-4-amino-1 -methylcyclohexan-1 -ol (67.9 mg, 0.525 mmol, Intermediate 21 , Astatech) was added, followed by the addition of N,N-diisopropylethylamine (0.092 mL, 0.525 mmol) and the reaction mixture was stirred for eight hours. The reaction mixture was concentrated under vacuum. The resulting semisolid residue was triturated with acetonitrile to give 7-cyclopropyl-N-((1 r,4r)-4-hydroxy-4-methylcyclohexyl)-1 ,6-naphthyridine-3- carboxamide (0.055 g, 0.161 mmol, 45.9 % yield) as an off white solid. 1H NMR (400 MHz, CD3SOCD3) δ 1 .00-1 .10 (m, 4 H), 1 .16 (s, 3 H), 1 .38-1 .54 (m, 4 H), 1 .56-1 .68 (m, 2 H), 1 .74- 1 .86 (m, 2 H), 2.34 (quin, J = 6 Hz, 1 H), 3.80-3.92 (m, 1 H), 4.32 (s, 1 H), 7.86 (s, 1 H), 8.57 (d, J = 8 Hz, 1 H), 8.88 (d, J = 2 Hz, 1 H), 9.33 (s, 1 H), 9.36 (d, J = 2 Hz, 1 H); LC-MS (LC-ES) M+H = 326.
  • 39
  • [ 177908-37-1 ]
  • 7-cyclopropyl-1,8-naphthyridine-3-carboxylic acid [ No CAS ]
  • 7-cyclopropyl-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-1,8-naphthyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55.0% N,N-Diisopropylethylamine (0.252 ml_, 1 .441 mmol) was added to 7-cyclopropyl-1 ,8- naphthyridine-3-carboxylic acid (0.0772 g, 0.360 mmol, Intermediate 4F) in N,N- dimethylformamide (1 .2 mL) at room temperature. Then, (1 r,4r)-4-amino-1 -methylcyclohexan- 1 -ol (0.047 g, 0.360 mmol, Intermediate 21 ) was added and the reaction mixture was stirred for five minutes. Then, n-propylphosphonic acid anhydride (0.429 mL, 0.721 mmol) was added and the reaction mixture was stirred for sixteen hours. The reaction mixture was concentrated. The resulting residue was purified by RP HPLC, eluting with acetonitrile:water with 0.1 % ammonium hydroxide (5:95 to 100:0), then further purified by silica gel chromatography, eluting with methanokethyl acetate (0:1 to 2:3) to give 7-cyclopropyl-N-((1 r,4r)-4-hydroxy-4- methylcyclohexyl)-1 ,8-naphthyridine-3-carboxamide (0.0679 g, 0.198 mmol, 55.0 % yield). 1H NMR (400 MHz, CD3SOCD3) δ 1 .16 (s, 3 H), 1 .10-1 .22 (m, 4 H), 1 .40-1 .56 (m, 4 H), 1 .56-1 .64 (m, 2 H), 1 .74-1 .86 (m, 2 H), 2.30-2.40 (m, 1 H), 3.80-3.92 (m, 1 H), 4.31 (s, 1 H), 7.63 (s, 1 H), 8.39 (d, J = 8 Hz, 1 H), 8.53 (d, J = 8 Hz, 1 H), 8.78 (d, J = 2 Hz, 1 H), 9.30 (d, J = 2 Hz, 1 H); LC-MS (LC-ES) M+H = 326.
  • 40
  • [ 177908-37-1 ]
  • [ 474659-26-2 ]
  • N-(trans-4-hydroxy-4-methylcyclohexyl)-7-methoxyquinoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20℃; for 16h; General procedure: N,N-Diisopropylethylamine (4.0 eq) was added to acid (1 eq) in solvent (dichloromethane, tetrahydrofuran, or N,N-dimethylformamide,0.05 to 0.2 M) at room temperature. Then, amine (1.0-2.0 eq) was added and the reaction mixture was stirred for five minutes. Then,n-propylphosphonic acid anhydride (2.0 eq) was added and the reaction mixture was stirred for sixteen hours. The reaction mixture was concentrated. The resulting residue was purified by RP HPLC or silica gel chromatography to give the quinoline-3-carboxamide (25%-86% yield).
  • 41
  • [ 177908-37-1 ]
  • [ 1332728-48-9 ]
  • C22H22ClFN6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 5.5h; General procedure: To a suspension of 9 (26.6 g, 76.3 mmol) in N,N-dimethylformamide (380 mL) was added 1-amino-2-methyl-propan-2-ol (8.16 g, 91.5 mmol) and triethylamine (31.9 mL, 228 mmol) at 0 C. The reaction mixture was stirred at room temperature for 5.5 h. Then the reaction mixture was diluted with cold water (1000 mL) and the mixture was stirred at room temperature for 1 h. The resulting precipitate was collected and washed with water. The precipitate was triturated with a mixture of diethyl ether and diisopropyl ether (1:1, 60 mL) to give the title compound (27.7 g, 83%) as a tan colored powder.
  • 42
  • [ 177908-37-1 ]
  • [ 1332729-85-7 ]
  • C23H25ClN6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 5.5h; General procedure: To a suspension of 9 (26.6 g, 76.3 mmol) in N,N-dimethylformamide (380 mL) was added 1-amino-2-methyl-propan-2-ol (8.16 g, 91.5 mmol) and triethylamine (31.9 mL, 228 mmol) at 0 C. The reaction mixture was stirred at room temperature for 5.5 h. Then the reaction mixture was diluted with cold water (1000 mL) and the mixture was stirred at room temperature for 1 h. The resulting precipitate was collected and washed with water. The precipitate was triturated with a mixture of diethyl ether and diisopropyl ether (1:1, 60 mL) to give the title compound (27.7 g, 83%) as a tan colored powder.
  • 43
  • [ 177908-37-1 ]
  • 2-cyclopropylthiazolo[4,5-b]pyridine-6-carboxylic acid [ No CAS ]
  • 2-cyclopropyl-N-((trans)-4-hydroxy-4-methylcyclohexyl)thiazolo[4,5-b]pyridine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% To a solution of 2-cyclopropylthiazolo[4,5-b]pyridine-6-carboxylic acid (30 mg, 0.136 mmol, Intermediate 4) in DMF (1 ml_) was added DIEA (0.031 ml_, 0.177 mmol), followed by HATU (62 mg, 0.163 mmol). After ~5 minutes, (trans)-4-amino-1 - methylcyclohexan-1 -ol (21 mg, 0.163 mmol) was added, followed by additional DIEA (0.031 ml_, 0.177 mmol). After ~45 min, water (~8 ml_) was slowly added to the reaction mixture. After stirring at rt overnight, the mixture was partitioned between EtOAc and satd. K2CO3 solution. To the aqueous phase was added some solid NaCI and then it was extracted 2X with EtOAc. The combined organic phases were washed 1X with a very small amount of satd. brine, dried over Na2S04, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with 5-70% (3:1 EtOAc:EtOH):hexanes gradient. The product was subsequently crystallized from CH2CI2:hexanes to give 2-cyclopropyl-N-((trans)-4- hydroxy-4-methylcyclohexyl)thiazolo[4,5-b]pyridine-6-carboxamide (38 mg, 0.109 mmol, 80% yield) as a white solid. 1H NMR (400 MHz, CD3SOCD3) d ppm 8.99 (d, J = 2 Hz, 1 H), 8.88 (d, J = 2 Hz, 1 H), 8.42 (d, J = 8 Hz, 1 H), 4.31 (s, 1 H), 3.77-3.94 (m, 1 H), 2.64 (tt, J = 8, 5 Hz, 1 H), 1 .74-1 .85 (m, 2 H), 1 .57-1 .67 (m, 2 H), 1 .39-1 .55 (m, 4 H), 1 .30-1 .38 (m, 2 H), 1 .21 -1 .29 (m, 2 H), 1 .16 (s, 3 H). MS: m/z 332 (M+H).
  • 44
  • [ 177908-37-1 ]
  • 2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-phenylpropanoic acid [ No CAS ]
  • 2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-(trans)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; at 20℃; for 15h; To a stirred solution of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (50 mg, 0.13 mmol) , HATU (54 mg, 0.14 mmol) and DIPEA (50 mg, 0.39 mmol) in THF (10 ml) was added trans-4-amino-1-methylcyclohexan-1-ol (17 mg, 0.13 mmol) . The reaction mixture was stirred at rt for 15h. After completion, the reaction mixture was diluted with EtOAc (30 ml) and then washed with H 2O (15 ml X 2) . The organic layer was dried over Na 2SO 4, filtered and then concentrated under reduced pressure to afford a residue. The residue was purified by prep-TLC with PE: EtOAc (1: 5) to afford the product (35.7 mg, 56%) . 1H NMR (400 MHz, DMSO-d6) δ 8.24 (s, 1H) , 8.00 (s, 2H) , 7.95 (s, 1H) , 7.38 (d, J = 4Hz, 1H) , 7.32-7.24 (m, 4H) , 7.14 (d, J = 4Hz, 2H) , 6.74 (dd, J = 8Hz, 4Hz, 1H) , 4.19 (s, 1H) , 3.75-3.65 (m, 1H) , 2.25 (s, 3H) , 1.75-1.66 (m, 1H) , 1.64-1.54 (m, 1H) , 1.40-1.29 (m, 6H) , 0.99 (s, 3H) ppm. MS: M/e 501 (M+1) +.
  • 45
  • [ 177908-37-1 ]
  • (S)-2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-phenylpropanoic acid [ No CAS ]
  • (S)-2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-(trans)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; at 20℃; for 15h; To a stirred solution of (S) -2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (50 mg, 0.13 mmol) , HATU (54 mg, 0.14 mmol) and DIPEA (50 mg, 0.39 mmol) in THF (15 ml) was added trans-4-amino-1-methylcyclohexan-1-ol (18 mg, 0.14 mmol) . The reaction mixture was stirred at rt for 15h. After completion, the reaction mixture was diluted with EtOAc (30 ml) and then washed with H 2O (15 ml X 2) . The organic layer was dried over Na 2SO 4, filtered and then concentrated under reduced pressure to afford a residue. The residue was purified by prep-TLC with PE: EtOAc (1: 5) to afford the product (36.6 mg, 57%) . 1H NMR (400 MHz, DMSO-d6) δ 8.24 (s, 1H) , 8.00 (s, 2H) , 7.95 (s, 1H) , 7.37 (d, J = 8Hz, 1H) , 7.33-7.24 (m, 4H) , 7.14 (d, J = 8Hz, 2H) , 6.80-6.70 (m, 1H) , 4.20 (s, 1H) , 3.79-3.55 (m, 1H) , 2.25 (s, 3H) , 1.75-1.66 (m, 1H) , 1.64-1.56 (m, 1H) , 1.40-1.29 (m, 6H) , 0.99 (s, 3H) ppm. MS: M/e 501 (M+1) +.
  • 46
  • [ 177908-37-1 ]
  • (R)-2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-phenylpropanoic acid [ No CAS ]
  • (R)-2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-(trans)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; at 20℃; for 15h; To a stirred solution of (R) -2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (50 mg, 0.13 mmol) , HATU (54 mg, 0.14 mmol) and DIPEA (50 mg, 0.39 mmol) in THF (15 ml) was added trans-4-amino-1-methylcyclohexan-1-ol (18 mg, 0.14 mmol) . The reaction mixture was stirred at rt for 15h. After completion, the reaction mixture was diluted with EtOAc (30 ml) and then washed with H 2O (15 ml X 2) . The organic layer was dried over Na 2SO 4, filtered and then concentrated under reduced pressure to afford a residue. The residue was purified by prep-TLC with PE: EtOAc (1: 5) to afford the product (40.4 mg, 63%) . 1H NMR (400 MHz, DMSO-d6) δ 8.24 (s, 1H) , 8.00 (s, 2H) , 7.95 (s, 1H) , 7.37 (d, J = 8Hz, 1H) , 7.33-7.24 (m, 4H) , 7.14 (d, J = 8Hz, 2H) , 6.74 (dd, J = 4Hz, 2Hz, 1H) , 4.20 (s, 1H) , 3.76-3.63 (m, 1H) , 2.25 (s, 3H) , 1.77-1.65 (m, 1H) , 1.62-1.53 (m, 1H) , 1.40-1.29 (m, 6H) , 0.99 (s, 3H) ppm. MS: M/e 501 (M+1) +.
  • 47
  • [ 177908-37-1 ]
  • [ 51940-64-8 ]
  • ethyl 2-chloro-4-(((1r,4r)-4-hydroxy-4-methylcyclohexyl)amino)pyrimidine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -5 - 25℃; for 18h;Inert atmosphere; DIPEA (17.53 mL, 100.62 mmol) was added dropwise to a mixture of (lr,4r)-4-amino-1-methylcyclohexan-1-ol (10.00 g, 77.40 mmol) and <strong>[51940-64-8]ethyl 2,4-dichloropyrimidine-5-carboxylate</strong>(17.11 g, 77.40 mmol) in acetonitrile (300 mL) at -5C over 5 min under air. The reaction mixture5 was stirred for 18 h, slowly allowing to warm to rt, then was concentrated in vacuo, diluted withEtOAc (200 mL), and washed with water then with sat. brine. The organic layer was dried overMgS04, filtered and concentrated in vacuo. The resulting crude product was purified by fcc, elutiongradient 0 to 50% EtOAc inn-heptane, to afford the title compound (17.85 g, 74%) as a whitesolid; 1H NMR (400 MHz, DMSO) 1.16 (3H, s), 1.32 (3H, t), 1.46- 1.58 (6H, m), 1.82- 1.94 (2H,10 m), 4.06 (lH, dq), 4.26 (lH, s), 4.32 (2H, q), 8.45 (lH, d), 8.61 (lH, s); m/z MH+ 314.
  • 48
  • [ 177908-37-1 ]
  • 2-chloro-4-(((1r,4r)-4-hydroxy-4-methylcyclohexyl)amino)pyrimidine-5-carboxylic acid [ No CAS ]
  • 49
  • [ 177908-37-1 ]
  • 2-chloro-9-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-7,9-dihydro-8H-purin-8-one [ No CAS ]
  • 50
  • [ 177908-37-1 ]
  • 2-chloro-9-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-7-methyl-7,9-dihydro-8H-purin-8-one [ No CAS ]
  • 51
  • [ 177908-37-1 ]
  • 9-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-7-methyl-2-((7-methylquinoxalin-6-yl)amino)-7,9-dihydro-8H-purin-8-one [ No CAS ]
  • 9-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-7-methyl-2-((7-methylquinoxalin-6-yl)amino)-7,9-dihydro-8H-purin-8-one [ No CAS ]
  • 52
  • [ 66336-42-3 ]
  • [ 177908-37-1 ]
  • 53
  • [ 66336-42-3 ]
  • [ 177906-46-6 ]
  • [ 177908-37-1 ]
  • 54
  • C7H13NO2 [ No CAS ]
  • [ 177906-46-6 ]
  • [ 177908-37-1 ]
  • 55
  • [ 4746-97-8 ]
  • [ 177908-37-1 ]
  • 56
  • [ 4746-97-8 ]
  • [ 177906-46-6 ]
  • [ 177908-37-1 ]
  • 57
  • [ 17429-02-6 ]
  • [ 177908-37-1 ]
  • 58
  • [ 17429-02-6 ]
  • [ 177906-46-6 ]
  • [ 177908-37-1 ]
  • 59
  • [ 177908-37-1 ]
  • 2-(4-((4-fluoro-3-methylphenyl)carbamoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl)-2-oxoacetic acid [ No CAS ]
  • N-(4-fluoro-3-methylphenyl)-5-(2-(((1r,4r)-4-hydroxy-4-methylcyclohexyl)amino)-2-oxoacetyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: HATU (90 mg, 0.24 mmol) was added to a solution of 1g (60 mg, 0.19) in DMA (0.75 mL) at 0 C. After 20 min, tert-butylamine (20 mg, 0.28) and DIPEA (50 mg, 0.38 mmol) in DMA (0.4 mL) were added. The reaction mixture was stirred at rt for 20 hrs. The reaction mixture was quenched with aqueous TFA (4%, 0.4 mL), then, extracted with EtOAc (10 mL). The organic layer was washed with water and brine, concentrated in vacuo, then, purified by reverse phase chromatography eluted with ACN and water, and dried using lyophilization to afford the title product as white solid. ESI-MS, m/z 360 (MH)+.
  • 60
  • [ 177908-37-1 ]
  • 7-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-3-(quinolin-4-yl)imidazo[1,2-b]pyridazine-6-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • N-((1R,4R)-4-hydroxy-4-methylcyclohexyl)-7-(4-(piperazin-1-yl)phenyl)-3-(quinolin-4-yl)imidazo[1,2-b]pyridazine-6-carboxamide trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of 7-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-3-(quinolin-4-yl)imidazo[1,2-b]pyridazine-6-carboxylic acid (20.0 mg, 0.036 mmol) in DMF (1.0 ml) was treated with HATU (55.2 mg, 0.145 mmol). The mixture was stirred at room temperature for 10 min, then <strong>[177908-37-1]cis-4-amino-1-methylcyclohexanol</strong> (48.9 mg, 0.378 mmol) was added followed by DIPEA (100.0 μL, 0.573 mmol). The reaction mixture was stirred to 50 C. for 16 h. After cooling to room temperature, the reaction was concentrated. The residue was treated with CH2Cl2 (2.0 mL) followed by TFA (2.0 mL). The mixture was stirred at room temperature for 15 min, and then concentrated. The residue was purified using prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min) to afford the desired product as its TFA salt. LCMS calculated for C33H36N7O2 (M+H)+: m/z=562.3. found: 562.3.
  • 61
  • [ 177908-37-1 ]
  • [ 32315-10-9 ]
  • 3-bromo-N-((4-(5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl)bicyclo[2.2.2]octan-1-yl)methyl)aniline [ No CAS ]
  • 1-(3-bromophenyl)-1-((4-(5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl)bicyclo[2.2.2]octan-1-yl)methyl)-3-((1R,4R)-4-hydroxy-4-methylcyclohexyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% A stirred solution of Intermediate 30A (15 mg, 0.035 mmol) and TEA (0.02 mL, 0.17 mmol) in DCM (3 mL) was cooled to 0 C. Triphosgene (10 mg, 0.03 mmol) as a solution in DCM (1 mL) was added to the reaction mixture. The reaction mixture was allowed to warm up to room temperature and stirred for 12 h. To the above reaction mixture, trans-4-Amino-1-methylcyclohexanol (5.46 mg, 0.04 mmol) was added and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure. The crude compound was purified via preparative LC/MS using following conditions: Column: Waters XBridge C18, 150 mm x 19 mm, 5- mm particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: a 2- minute hold at 18% B, 18-62% B over 25 minutes, then a 5-minute hold at 100% B; Flow Rate: 15 mL/min; Column Temperature: 25 C. Fraction collection was triggered by signals. Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compound (6 mg, 10.84 µmol, 31% yield) as an off white solid. 1H NMR (400MHz, DMSO-d6) d 7.54 (d, J = 1.7 Hz, 1H), 7.44-7.38 (m, 1H), 7.37-7.27 (m, 2H), 5.44 (d, J = 7.8 Hz, 1H), 4.20 (s, 1H), 3.53 (s, 2H), 3.49-3.42 (m, 1H), 2.14 (t, J = 19.7 Hz, 3H), 1.82-1.68 (m, 6H), 1.65-1.53 (m, 2H), 1.45-1.23 (m, 12H), 1.06 (s, 3H). FXR EC50 (nM) = 150; MS (ESI) 581 (M+H).
  • 62
  • [ 177908-37-1 ]
  • 4-(6-fluoro-4-iodopyridin-2-yl)morpholine [ No CAS ]
  • (1r,4r)-4-[4-iodo-6-(morpholin-4-yl)pyridin-2-yl]amino}-1-methylcyclohexan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 150℃; for 16h; To a stirred mixture of 4-(6-fluoro-4-iodopyridin-2-yl)morpholine (300 mg, 0.974 mmol) and K2CO3(404 mg, 2.921 mmol) in NMP (3 mL) was added (1R,4R)-4-amino-1- methylcyclohexan-1-ol (189 mg, 1.461 mmol) at room temperature . The resulting mixture was stirred for 16 h at 150 C. The mixture was allowed to cool down to room temperature. The residue was purified by reverse flash chromatography with the following conditions: column, C18 silica gel; mobile phase, CH3CN in water, 30% to 70% gradient in 20 min; detector, UV 254 nm to afford (1R,4R)-4-((4-iodo-6-morpholinopyridin-2-yl)amino)-1- methylcyclohexan-1-ol (320 mg, 79%) as a light brown solid. MS ESI calculated for C16H24IN3O2 [M + H]+418.09 found 418.00.1H NMR (300 MHz, chloroform-d) δ 6.28 (s, 1H), 6.18 (s, 1H), 4.27 (s, 1H), 3.84-3.75 (m, 4H), 3.63-3.39 (m, 5H), 2.02-1.36 (m, 8H), 1.31 (s, 3H), 1.27 (s, 1H).
  • 63
  • [ 177908-37-1 ]
  • 4-(6-fluoro-4-iodopyridin-2-yl)morpholine [ No CAS ]
  • (S)-N-(3-(2-(((1R,4S)-4-hydroxy-4-methylcyclohexyl)amino)-6-morpholinopyridin-4-yl)-4-methylphenyl)-3-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide [ No CAS ]
  • 64
  • [ 177908-37-1 ]
  • 2-(1H-imidazol-1-yl)-N-((1r,4r)-4-methoxy-4-methylcyclohexyl)pyrimidine-4-carboxamide [ No CAS ]
  • 65
  • [ 177908-37-1 ]
  • (1r,4r)-4-methoxy-4-methylcyclohexan-1-amine [ No CAS ]
  • 66
  • [ 177908-37-1 ]
  • [ 100-39-0 ]
  • (1r,4r)-4-(dibenzylamino)-1-methylcyclohexan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With potassium carbonate; In N,N-dimethyl-formamide; at 75℃; for 16h; To a stirred solution of <strong>[177908-37-1](1r,4r)-4-amino-1-methylcyclohexan-1-ol</strong> (359 mg, 2.77 mmol, cas no- 177908-37-1) in acetonitrile (10 mL), potassium carbonate (1.15 g, 8.33 mmol) and benzyl bromide (0.66 mL, 5.55 mmol) were added at RT and the reaction mixture was heated at 75 C for 16 h. After completion, the reaction mixture was quenched with water (50 mL) and extracted with EtOAc (100 mL). The combined organic layer was washed with water (3 x 50 mL), dried over anhydrous Na2SO4, filtered and the filtrate was concentrated under vacuum to get the title compound. Yield: 61% (531 mg, white solid).1H NMR (400 MHz, DMSO-d6): δ 7.36-7.17 (m, 8H), 4.18 (s, 1H), 3.53 (s, 4H), 2.44-2.28 (m, 3H), 1.71-1.66 (m, 2H), 1.57-1.53 (m, 2H), 1.49-1.36 (m, 2H), 1.27-1.17 (m, 2H), 1.10 (s, 3H). LCMS: (Method A) 296.2 (M-OH), Rt.1.23 min.
  • 67
  • [ 177908-37-1 ]
  • [ 100-39-0 ]
  • (1r,4r)-N,N-dibenzyl-4-methoxy-4-methylcyclohexan-1-amine [ No CAS ]
  • 68
  • [ 149849-93-4 ]
  • [ 177908-37-1 ]
  • 2-chloro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.23 g With triethylamine; In tetrahydrofuran; at 0 - 20℃; To a stirred solution of 2-chloropyrimidine-4-carbonyl chloride (0.2 g, 1.13 mmol) and TEA (0.47 mL, 3.39 mmol) in THF (10 mL) at 0 C was added <strong>[177908-37-1](1r,4r)-4-amino-1-methylcyclohexan-1-ol</strong> (0.195 g, 1.35 mmol, CAS: 177908-37-1), and the reaction mixture was stirred at RT overnight. After completion (monitored by TLC), the reaction mixture was quenched with sat. aq. NaHCO3 solution (10 mL). The resulting suspension was extracted with EtOAc (2 x 25 mL). The combined organic layer was washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4 and concentrated under vacuum to afford the title compound. Yield: 75% (0.23 g, Off white solid).1H NMR (400 MHz, DMSO-d6): δ 9.00 (d, J = 2.0, 6.8 Hz, 1H), 8.69 (d, J = 11.6 Hz, 1H), 8.00 (dd, J = 2.0, 6.8 Hz, 1H), 4.31 (d, J = 1.2 Hz, 1H), 3.88-3.75 (m, 1H), 1.67-1.39 (m, 8H), 1.24 (s, 3H). LCMS: (Method C) 270.0 (M+H), Rt.1.40 min.
  • 69
  • [ 177908-37-1 ]
  • C21H22N6O5S [ No CAS ]
  • 2-amino-5-{2-[(1S)-1-cyclopropylethyl]-7-methanesulfonamido-1-oxo-2,3-dihydro-1H-isoindol-5-yl}-N-[trans-4-hydroxy-4-methylcyclohexyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 70
  • [ 177908-37-1 ]
  • C19H17F3N6O5S [ No CAS ]
  • 2-amino-5-{7-methanesulfonamido-1-oxo-2-[(2S)-1,1,1-trifluoropropan-2-yl]-2,3-dihydro-1H-isoindol-5-yl}-N-[cis-4-hydroxy-4-methylcyclohexyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 71
  • [ 177908-37-1 ]
  • 2-amino-5-{2-[(1S)-1-cyclopropylethyl]-7-methyl-1-oxo-2,3-dihydro-1H-isoindol-5-yl}pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [ No CAS ]
  • 2-amino-5-{2-[(1S)-1-cyclopropylethyl]-7-methyl-1-oxo-2,3-dihydro-1H-isoindol-5-yl}-N-[trans-4-hydroxy-4-methylcyclohexyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 72
  • [ 177908-37-1 ]
  • 2-azido-4-methoxy-5-nitrobenzaldehyde [ No CAS ]
  • cis-4-(6-methoxy-5-nitro-indazole-2-yl)-1-methylcyclohexanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.6% With acetic acid; In ethanol; at 0 - 77℃; for 5h;Large scale; The ethanol solution of 2-azido-4-methoxy-5-nitrobenzaldehyde in the above-mentioned 20L double-layer glass reactor (calculated at 100% yield, i.e., 5.00mol) was cooled and cooled, the reactor temperature was maintained to 0-5 C, and acetic acid (900.00g) and <strong>[177908-37-1]cis-4-amino-1-methylcyclohexanol</strong> (645.00g) were added sequentially, and then heated up to the reaction temperature at 72-77 C, and the system was kept warm for 5 hours. After the reaction system is cooled to 30-40 C, water (6L) is added, the reaction mixture is concentrated under vacuum, the reaction mixture is concentrated to a certain volume (about 7L), cooling and cooling, keeping the temperature in the reactor to 20-25 C, filtering, the filter cake is rinsed with a small amount of water, added to the reactor, after recrystallization with ethanol and n-heptane, filtered and dried to obtain cis-4- (6-methoxy-5-nitro - indazole-2-yl)-1-methyl - cyclohexanol (1366.40g, yield: 89.6%).
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