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[ CAS No. 177906-46-6 ] {[proInfo.proName]}

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Product Details of [ 177906-46-6 ]

CAS No. :177906-46-6 MDL No. :MFCD18791201
Formula : C7H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :KUKASNZJTIKRMH-UHFFFAOYSA-N
M.W :129.20 Pubchem ID :18331273
Synonyms :

Safety of [ 177906-46-6 ]

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 [ 177906-46-6 ]

* 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 [ 177906-46-6 ]

[ 177906-46-6 ] Synthesis Path-Downstream   1~35

YieldReaction ConditionsOperation in experiment
IX cis-4-Amino-1-methylcyclohexanol The following compound is obtained analogously to Example IX:
  • 2
  • (1s,4s)-4-(dibenzylamino)-1-methylcyclohexan-1-ol [ No CAS ]
  • [ 177906-46-6 ]
YieldReaction ConditionsOperation in experiment
91.8% With hydrogen; palladium(II) hydroxide In ethanol at 20℃; for 16h; Inert atmosphere; 1A (ls,4s)-4-Amino-1-methylcyclohexan-1-ol Four equal batches of (1 s,4s)-4-dibenzylamino- 1 -methylcyclohexan- 1 -ol (each batch was 15 g, total 60 g) were separately debenzylated as follows: To (ls,4s)-4-dibenzylamino-1- methylcyclohexan-1-ol (15 g, 193.9 mmol) in ethanol (450 mL) was added 10% palladiumhydroxide (15 g, 50% wet catalyst). The reaction mixtures were flushed with nitrogen followed by hydrogen gas and stirred under an atmosphere of hydrogen for 16 hours at room temperature. The solution was filtered through celite and which was washed with additional ethyl acetate. The filtrates from all four batches were combined and evaporated under reduced pressure to afford the title compound (23 g, 91.8 % yield).The compound was used without further purification in the next step. 1H NMR (400 MHz, ODd3) O: 2.6 (m, 1H), 1.74-1.56 (m, 4H), 1.5-1.3 (m, 7H), 1.21 (5,3H).
91.8% With hydrogen; palladium(II) hydroxide In ethanol; water at 20℃; for 16h; B Synthesis B (1 s,4s)-4-Amino-1 -methylcyclohexan-1 -ol Synthesis B (1 s,4s)-4-Amino-1 -methylcyclohexan-1 -ol Four equal batches of (1 s,4s)-4-dibenzylamino-1 -methylcyclohexan-1 -ol (each batch was 15 g, total 60 g) were separately debenzylated as follows: To (1 s,4s)-4-dibenzylamino-1- methylcyclohexan-1-ol (15 g, 193.9 mmol) in ethanol (450 mL) was added 10% palladium hydroxide (15 g, 50% wet catalyst). The reaction mixtures were flushed with nitrogen followed by hydrogen gas and stirred under an atmosphere of hydrogen for 16 hours at room temperature. The solution was filtered through celite and which was washed with additional ethyl acetate. The filtrates from all four batches were combined and evaporated under reduced pressure to afford the title compound (23 g, 91 .8 % yield). The compound was used without further purification in the next step. 1H NMR (400 MHz, CDCI3) δ: 2.6 (m, 1 H), 1.74 - 1.56 (m, 4H), 1.5 - 1 .3 (m, 7H), 1.21 (s, 3H).
  • 4
  • [ 177906-46-6 ]
  • [ 59477-37-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate 2: potassium hydrogensulfate; sulfuric acid 3: hydrazine
  • 5
  • [ 177906-46-6 ]
  • [ 291756-09-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate 2: potassium hydrogensulfate; sulfuric acid 3: hydrazine 4: triethylamine / dichloromethane
  • 6
  • [ 177906-46-6 ]
  • [ 1403864-55-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate 2: potassium hydrogensulfate; sulfuric acid 3: hydrazine 4: triethylamine / dichloromethane 5: diborane / tetrahydrofuran
  • 7
  • [ 177906-46-6 ]
  • [ 22509-74-6 ]
  • C15H17NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With potassium carbonate 10 Example 10: Route 6 for synthesis of (lR,2R,5R)-5-amino-2-methylcyclohexanol and its HCl salt Example 10: Route 6 for synthesis of (lR,2R,5R)-5-amino-2-methylcyclohexanol and its HCl salt Route 6 can be used to make (lR,2R,5R)-5-amino-2-methylcyclohexanol and its HCl salt starting from amine (27). As described in International Patent Application publication WO2012/145569, protection of the amine (27) with compound (28) gave phthalimide (29). Dehydration with acid, such as H2SO4/KHSO4 gave alkene (30). Deprotection of (30) afforded amine (31). The amine was protected to give the racemic (32). The trans hydroxy 1 group was installed by hydroboration/oxidation of compound (32) to give a mixture of four diastereomers (9 a-d). Compound 9a is purified by chiral SFC as described in route 1. Deprotection of compound 9a with acid, such as HCl, provides (lR,2R,5R)-5-amino-2-methylcyclohexanol HCl salt (A).
  • 8
  • [ 177906-46-6 ]
  • [ 22509-74-6 ]
  • [ 25577-22-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate 2: potassium hydrogensulfate; sulfuric acid
  • 9
  • [ 177906-46-6 ]
  • [ 98-58-8 ]
  • 4-bromo-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; I Synthesis I 4-Bromo-N-((1 s,4s)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide Synthesis I 4-Bromo-N-((1 s,4s)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide To a solution of (1 s,4s)-4-amino-1-methylcyclohexan-1 -ol (2 g, 15.48 mmol) in dichloromethane (100 mL) was added diisopropylethylamine (5 g, 38.68 mmol) and the reaction mixture was cooled to 0°C. 4-Bromobenzene-1-sulfonyl chloride (4.35 g, 17.02 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 in 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 (3.6 g, 67%). MS (ESI) m/z 346[M-H].
  • 10
  • [ 177906-46-6 ]
  • 3-fluoro-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 2.17 h / 110 °C / Inert atmosphere
  • 11
  • [ 177906-46-6 ]
  • 4'-cyano-2-fluoro-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 2.17 h / 110 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 8.17 h / 80 °C / Inert atmosphere
  • 12
  • [ 177906-46-6 ]
  • 2',4',5'-trifluoro-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 4.17 h / 100 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 6.17 h / 110 °C / Inert atmosphere
  • 13
  • 4-bromo-3-fluorobenzene-1-sulfonyl chloride [ No CAS ]
  • [ 177906-46-6 ]
  • 4-bromo-3-fluoro-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; K Synthesis K 4-Bromo-3-fluoro-/V-((1 s,4s)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide Synthesis K 4-Bromo-3-fluoro-/V-((1 s,4s)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide To a solution of (1 s,4s)-4-amino-1 -methylcyclohexan-1 -ol (1 g, 7.74 mmol) in dichloromethane (80 ml_), diisopropylethylamine (2.5 g, 19.3 mmol) was added and the reaction mixture was cooled to 0°C. 4-Bromo-3-fluorobenzenesulfonyl chloride (2.33 g, 8.5 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 (1.6 g, 56%). 1H NMR (400 MHz, DMSO-d6) δ: 8.03 - 7.90 (m, 1 H), 7.87 - 7.70 (m, 2 H), 7.61 - 7.54 (m, 1 H), 2.97 - 2.84 (m, 1 H), 1.59 - 1.37 (m, 4 H), 1.36 - 1.14 (m, 4 H), 1 .01 (s, 3 H).
  • 14
  • [ 177906-46-6 ]
  • [ 1428368-75-5 ]
  • (1s,4s)-4-((4-(3,5-dimethylisoxazol-4-yl)-2-nitrophenyl)amino)-1-methylcyclohexan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In acetonitrile for 1h; Reflux; (2s, s)-4-((4-(3,5-dimethylisoxazol-4-yl)-2-nitrophenyl)amino)-l-methylcyclohexan- l-ol B15) 4-(4-Fluoro-3-nitrophenyl)-3,5-dimethylisoxazole (750 mg, 3.18 mmol), (ls,4s) - amino-1 -methyl cyclohexanol (500 mg, 3.87 mmol) and potassium carbonate (600 mg, 4.34 mmol) were heated to reflux in acetonitrile (10 mL) for 1 h. The mixture was diluted with water (50 mL) then the precipitate was collected by filtration. The crude product was purified by chromatography on the Companion (40 g column, 0-50% EtOAc/isohexane) to afford (/s,¥s)-4-((4-(3,5-dimethylisoxazol-4-yl)-2- nitrophenyl)amino)-l -methyl cyclohexanol (855 mg, 74%) as an orange solid; Rt 2.15 min (method 1); m/z 346 (M+H)+ (ES+).
  • 15
  • [ 177906-46-6 ]
  • 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)-(cis)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃; for 15h; 69 Example 69: 2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-(cis)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylpropanamide 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 (15 ml) was added cis-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 (39.2 mg, 61%) . 1H NMR (400 MHz, DMSO-d6) δ 8.21 (s, 1H) , 7.95 (s, 3H) , 7.47 (d, J = 8Hz, 1H) , 7.31-7.23 (m, 4H) , 7.17 (d, J = 8Hz, 2H) 6.73 (dd, J= 4, 2Hz, 1H) , 3.93 (s, 1H) , 3.61-3.52 (m, 1H) , 2.27 (s, 3H) , 1.56-1.43 (m, 6H) , 1.32-1.25 (m, 2H) , 1.06 (s, 3H) ppm. MS: M/e 501 (M+1) +.
  • 16
  • [ 177906-46-6 ]
  • (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)-(cis)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃; for 15h; 69A Example 69A: (S)-2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-(cis)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylpropanamide 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 (100 mg, 0.26 mmol) , HATU (108 mg, 0.28 mmol) and DIPEA (100 mg, 0.78 mmol) in THF (15 ml) was added cis-4-amino-1-methylcyclohexan-1-ol (33 mg, 0.26 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: 4) to afford the product (70.1 mg, 54%) . 1H NMR (400 MHz, DMSO-d6) δ 8.21 (s, 1H) , 8.06-7.88 (m, 3H) , 7.47 (d, J = 8Hz, 1H) , 7.31-7.22 (m, 4H) , 7.16 (d, J = 8Hz, 2H) , 6.79-6.70 (m, 1H) , 3.93 (s, 1H) , 3.64-3.52 (m, 1H) , 2.26 (s, 3H) , 1.56-1.45 (m, 6H) , 1.32-1.22 (m, 2H) , 1.05 (s, 3H) ppm. MS: M/e 501 (M+1) +.
  • 17
  • [ 177906-46-6 ]
  • 2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-phenylacetic 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)-(cis)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃; for 15h; 96 Example 96: 2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-(cis)-N-(4-hydroxy-4-methylcyclohexyl)-2-phenylacetamide 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-phenylacetic acid (50 mg, 0.13 mmol) , HATU (56 mg, 0.15 mmol) and DIPEA (52 mg, 0.40 mmol) in THF (15 ml) was added cis-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 DCM: MeOH (30: 1) to afford the product (26.2 mg, 40%) . 1H NMR (400 MHz, DMSO-d6) δ 8.20 (s, 1H) , 8.16 (s, 2H) , 7.95 (s, 1H) , 7.91 (d, J = 8Hz, 1H) , 7.42-7.32 (m, 5H) , 7.25 (d, J = 4Hz, 1H) , 6.73 (dd, J = 4Hz, 2Hz, 1H) , 6.38 (s, 1H) , 4.01 (s, 1H) , 3.57-3.47 (m, 1H) , 1.56-1.43 (m, 5H) , 1.34-1.28 (m, 3H) , 1.07 (s, 3H) ppm. MS: M/e 487 (M+1) +.
  • 18
  • [ 177906-46-6 ]
  • 2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-(2-methoxyphenyl)propanoic 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)-N-((cis)-4-hydroxy-4-methylcyclohexyl)-2-(2-methoxyphenyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h; 140 Example 140: 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -N- ( (cis) -4-hydroxy-4-methylcyclohexyl) -2- (2-methoxyphenyl) propanamide To a mixture of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2- (2-methoxyphenyl) propanoic acid (50 mg, 0.12 mmol) , (cis) -4-amino-1-methylcyclohexan-1-ol (19 mg, 0.15 mmol) , DIPEA (65 mg, 0.5 mmol) in DMF (2 mL) was added HATU (57 mg, 0.15 mmol) at rt and the mixture was stirred at rt for 16 hrs. The mixture was diluted with 20 mL of EtOAc, washed with brine (10 mL x 3) , dried over Na 2SO 4, concentrated and the resulted oil was purified by prep-TLC (EtOAc) to give the title product (39 mg, yield: 61%) . 1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H) , 8.07 -7.87 (m, 3H) , 7.34 -7.21 (m, 3H) , 7.05 (d, J = 7.6 Hz, 1H) , 6.83 (t, J = 7.2 Hz, 1H) , 6.78 -6.71 (m, 1H) , 6.53 (d, J = 6.8 Hz, 1H) , 3.96 (s, 1H) , 3.66 (s, 3H) , 3.58 -3.40 (m, 1H) , 2.25 (s, 3H) , 1.68 -1.58 (m, 1H) , 1.55 -1.38 (m, 4H) , 1.35 -1.21 (m, 3H) , 1.05 (s, 3H) . MS: M/e 531 (M+1) +.
  • 19
  • [ 177906-46-6 ]
  • [ 51940-64-8 ]
  • ethyl 2-chloro-4-(((1s,4s)-4-hydroxy-4-methylcyclohexyl)amino)pyrimidine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -5℃; for 2.25h;Inert atmosphere; DIPEA (8.76 mL, 50.31 mmol) was added dropwise to a mixture of (ls,4s)-4-amino-1-methylcyclohexan-1-ol (5.00 g, 38.70 mmol) and ethyl2,4-dichloropyrimidine-5-carboxylate (8.55g, 38.70 mmol) in acetonitrile (143 mL) at -5C over a period of 15 min under air. The reaction5 mixture was stirred for 2 h, then was slowly allowed to warm tort, concentrated in vacuo, dilutedwith EtOAc (200 mL), and washed with water then with sat. brine. The organic layer was driedover MgS04, filtered and concentrated in vacuo. The resulting crude mixture was suspended inDCM (20 mL ), and the resulting solid was isolated by filtration and was washed with DCM ( 5 mL)to afford title compound (3.8 g). The filtrate was purified by fcc, elution gradient 0 to 70% EtOAc10 inn-heptane, to afford additional title compound (5.3 g). Both batches were combined to afford thetitle compound (9.10 g, 75%) as a white solid; 1H NMR (400 MHz, DMSO) 1.13 (3H, s), 1.32 (3H,t), 1.43 (2H, td), 1.53 - 1.61 (2H, m), 1.69 (4H, tt), 3.85- 3.99 (lH, m), 4.15 (lH, s), 4.32 (2H, q),8.27 (lH, d), 8.62 (lH, s); m/zMH+ 314.
  • 20
  • [ 177906-46-6 ]
  • 2-chloro-4-(((1s,4s)-4-hydroxy-4-methylcyclohexyl)amino)pyrimidine-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2.25 h / -5 °C / Inert atmosphere 2: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 17 - 25 °C / Inert atmosphere
  • 21
  • [ 177906-46-6 ]
  • 2-chloro-9-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-7,9-dihydro-8H-purin-8-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2.25 h / -5 °C / Inert atmosphere 2: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 17 - 25 °C / Inert atmosphere 3: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran; water / 24 h / 17 - 80 °C / Inert atmosphere
  • 22
  • [ 177906-46-6 ]
  • 2-chloro-9-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-7-methyl-7,9-dihydro-8H-purin-8-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2.25 h / -5 °C / Inert atmosphere 2: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 17 - 25 °C / Inert atmosphere 3: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran; water / 24 h / 17 - 80 °C / Inert atmosphere 4: sodium hydroxide / tetrahydrofuran / 3 h / 17 - 25 °C / Inert atmosphere
  • 23
  • [ 177906-46-6 ]
  • 9-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-7-methyl-2-((7-methylcinnolin-6-yl)amino)-7,9-dihydro-8H-purin-8-one [ No CAS ]
  • 9-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-7-methyl-2-((7-methylcinnolin-6-yl)amino)-7,9-dihydro-8H-purin-8-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2.25 h / -5 °C / Inert atmosphere 2: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 17 - 25 °C / Inert atmosphere 3: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran; water / 24 h / 17 - 80 °C / Inert atmosphere 4: sodium hydroxide / tetrahydrofuran / 3 h / 17 - 25 °C / Inert atmosphere 5: [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; caesium carbonate / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere
  • 24
  • [ 66336-42-3 ]
  • [ 177906-46-6 ]
  • [ 177908-37-1 ]
  • 25
  • C7H13NO2 [ No CAS ]
  • [ 177906-46-6 ]
  • [ 177908-37-1 ]
  • 26
  • [ 4746-97-8 ]
  • [ 177906-46-6 ]
  • [ 177908-37-1 ]
  • 27
  • [ 17429-02-6 ]
  • [ 177906-46-6 ]
  • [ 177908-37-1 ]
  • 28
  • [ 177906-46-6 ]
  • 4-(1-(2-chloro-4-formylphenyl)-1H-pyrazol-4-yl)-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidine-5-carbonitrile [ No CAS ]
  • 4-(1-(2-chloro-4-((((1s,4s)-4-hydroxy-4-methylcyclohexyl)amino)methyl)phenyl)-1H-pyrazol-4-yl)-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (1s,4s)-4-amino-1-methylcyclohexan-1-ol; 4-(1-(2-chloro-4-formylphenyl)-1H-pyrazol-4-yl)-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidine-5-carbonitrile In methanol at 70℃; for 1h; Stage #2: With sodium cyanoborohydride In methanol at 70℃; for 2h; 173 4-(l-(2-Chloro-4-((((ls,4s)-4-hydroxy-4- methylcyclohexyl)amino)methyl)phenyl)-l/ -pyrazol-4-yl)-2-((l- (methylsulfonyl)piperidin-4-yl)amino)pyrimidine-5-carbonitrile To a mixture of 4-( 1 -(2-chl oro-4-formyl phenyl )-l//-pyrazol-4-yl)-2-((l - (methylsulfonyl)piperidin-4-yl)amino)pyrimidine-5-carbonitrile ( Example 99, Step 1, 10 mg, 0.021 mmol) in methanol (1 mL) was added (ls,4s)-4-amino-l- methylcyclohexan-l-ol (4 mg, 0.03 mmol) and the reaction mixture was stirred at 70 °C for 1 hour. Sodium cyanoborohydride (3.9 mg, 0.062 mmol) was then added, and the reaction mixture was stirred at 70 °C for 2 hours. After cooling to r.t., the reaction mixture was then diluted with methanol and purified with prep-LCMS (Sunfire Cl 8 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C28H36CIN8O3S (M+H)+: m/z = 599.2; Found: 599.3.
  • 29
  • [ 177906-46-6 ]
  • 4-(6-fluoro-4-iodopyridin-2-yl)morpholine [ No CAS ]
  • (1s,4s)-4-[4-iodo-6-(morpholin-4-yl)pyridin-2-yl]amino}-1-methylcyclohexan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; for 16h; 36.36A Preparation 36A: (1S,4S)-4-((4-iodo-6-morpholinopyridin-2-yl)amino)-1-methylcyclohexan- 1-ol To a stirred mixture of 4-(6-fluoro-4-iodopyridin-2-yl)morpholine (300 mg, 0.974 mmol) and K2CO3( 407 mg, 2.921 mmol) in NMP (3 mL) was added (cis)-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 (1S,4S)-4-((4-iodo-6-morpholinopyridin-2-yl)amino)-1-methylcyclohexan-1-ol (290 mg, 71%) as a light brown solid. MS ESI calculated for C16H24IN3O2418.09, found 417.95. 1H NMR (300 MHz, chloroform-d) δ 6.26 (s, 1H), 6.16 (s, 1H), 4.24 (d, J = 8.0 Hz, 1H), 3.84- 3.75 (m, 4H), 3.45-3.42 (m, 5H), 2.00-1.40 (m, 8H), 1.29 (s, 3H), 1.13 (s, 1H).
  • 30
  • [ 177906-46-6 ]
  • 4-(6-fluoro-4-iodopyridin-2-yl)morpholine [ No CAS ]
  • (3S)-N-{4-methyl-3-[2-(morpholin-4-yl)-6-[(1s,4s)-4-hydroxy-4-methylcyclohexyl]amino}pyridin-4-yl]phenyl}-3-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 16 h / 150 °C 2: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 70 °C / Inert atmosphere
  • 31
  • [ 177906-46-6 ]
  • 2-(1H-imidazol-1-yl)pyrimidine-4-carboxylic acid [ No CAS ]
  • N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-2-(1H-imidazol-1-yl)pyrimidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
142 mg Stage #1: 2-(1H-imidazol-1-yl)pyrimidine-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: (1s,4s)-4-amino-1-methylcyclohexan-1-ol In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; 55.2 Step 2: N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-2-(1H-imidazol-1-yl)pyrimidine-4-carboxamide To a stirred solution of 2-(1H-imidazol-1-yl)pyrimidine-4-carboxylic acid (200 mg, 1.05 mmol) in DMF (3 mL) at 0 C, were added HATU (599 mg, 1.57 mmol) followed by DIPEA (0.9 mL, 5.25 mmol) under nitrogen atmosphere and the reaction mixture was stirred at 0 C for 5 min. Then (1s,4s)-4-amino-1-methylcyclohexan-1-ol (135.8 mg, 1.05 mmol, CAS: 177906-46-6) was added and the reaction mixture was stirred at RT overnight. After completion (starting material was consumed according to TLC), the reaction mixture was diluted with water (30 mL) and extracted with 10% MeOH in DCM (50 mL). The organic layer was dried over anhydrous Na2SO4, filtered and the filtrate was concentrated under vacuum. The resulting crude product was purified by Grace reverse phase purification (Method A). The prep-fraction was concentrated under reduced pressure, the residue was diluted with 10% MeOH in DCM (50 mL) and washed with 10% aq. NaHCO3 solution (20 mL) followed by water (2 x 20 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and finally lyophilized to get the title compound. Yield: 30% (142 mg, Off white solid).1H NMR (400 MHz, DMSO-d6): δ 9.05 (d, J = 5.2 Hz, 1H), 9.01-9.00 (m, 1H), 8.96 (d, J = 8.8 Hz, 1H), 8.27-8.27 (m, 1H), 7.91 (d, J = 4.8 Hz, 1H), 7.17-7.16 (m, 1H), 4.17 (s, 1H), 3.85-3.78 (m, 1H), 2.08-1.88 (m, 2H), 1.63-1.58 (m, 2H), 1.54-1.51 (m, 2H), 1.43-1.35 (m, 2H), 1.14 (s, 3H). LCMS: (Method A) 302.1 (M+H), Rt.0.51 min. HPLC: (Method A) Rt.1.88 min.
  • 32
  • [ 177906-46-6 ]
  • 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-[cis-4-hydroxy-4-methylcyclohexyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 40℃; for 2h; Inert atmosphere;
  • 33
  • [ 177906-46-6 ]
  • (S)-2-amino-5-(7-(benzylthio)-1-oxo-2-(1,1,1-trifluoropropan-2-yl)isoindolin-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [ No CAS ]
  • C32H33F3N6O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 40℃; for 2h; Inert atmosphere;
  • 34
  • [ 177906-46-6 ]
  • (S)-2-amino-5-(2-(1-cyclopropylethyl)-1-oxo-7-(trifluoromethoxy)isoindolin-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [ No CAS ]
  • 2-amino-5-{2-[(1S)-1-cyclopropylethyl]-1-oxo-7-(trifluoromethoxy)-2,3-dihydro-1H-isoindol-5-yl}-N-[(1s,4s)-4-hydroxy-4-methylcyclohexyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; 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 40℃; for 2h;
  • 35
  • [ 177906-46-6 ]
  • (S)-2-amino-5-(2-(1-cyclopropylethyl)-7-(difluoromethoxy)-1-oxoisoindolin-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [ No CAS ]
  • 2-amino-5-{2-[(1S)-1-cyclopropylethyl]-7-(difluoromethoxy)-1-oxo-2,3-dihydro-1H-isoindol-5-yl}-N-[(1s,4s)-4-hydroxy-4-methylcyclohexyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; 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 40℃; for 2h;
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