[ CAS No. 177906-46-6 ]

Name: 177906-46-6|cis--4-Amino-1-methylcyclohexanol|98%
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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:	Ⅲ
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

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: IP GROUP PLC - WO2014/207445, 2014, A1 Location in patent: Page/Page column 46
[2]Current Patent Assignee: IP GROUP PLC - WO2016/97001, 2016, A1 Location in patent: Page/Page column 44-45

3
[ 177906-46-6 ]
2-(methylsulfonyl)-4-(1-(tetrahydro-2H-pyran-2-yl)-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-4-yl)pyrimidine [ No CAS ]
C₂₃H₃₀F₃N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane at 160℃; for 1h; Microwave irradiation;

Reference： [1]Wityak, John; McGee, Kevin F.; Conlon, Michael P.; Song, Ren Hua; Duffy, Bryan C.; Clayton, Brent; Lynch, Michael; Wang, Gwen; Freeman, Emily; Haber, James; Kitchen, Douglas B.; Manning, David D.; Ismail, Jiffry; Khmelnitsky, Yuri; Michels, Peter; Webster, Jeff; Irigoyen, MacArena; Luche, Michele; Hultman, Monica; Bai, Mei; Kuok, Iokteng D.; Newell, Ryan; Lamers, Marieke; Leonard, Philip; Yates, Dawn; Matthews, Kim; Ongeri, Lynette; Clifton, Steve; Mead, Tania; Deupree, Susan; Wheelan, Pat; Lyons, Kathy; Wilson, Claire; Kiselyov, Alex; Toledo-Sherman, Leticia; Beconi, Maria; Muñoz-Sanjuan, Ignacio; Bard, Jonathan; Dominguez, Celia [Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 2967 - 2987]

4
[ 177906-46-6 ]
[ 59477-37-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate 2: potassium hydrogensulfate; sulfuric acid 3: hydrazine

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/116755, 2015, A2

5
[ 177906-46-6 ]
[ 291756-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate 2: potassium hydrogensulfate; sulfuric acid 3: hydrazine 4: triethylamine / dichloromethane

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/116755, 2015, A2

6
[ 177906-46-6 ]
[ 1403864-55-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate 2: potassium hydrogensulfate; sulfuric acid 3: hydrazine 4: triethylamine / dichloromethane 5: diborane / tetrahydrofuran

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/116755, 2015, A2

7
[ 177906-46-6 ]
[ 22509-74-6 ]
C₁₅H₁₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/116755, 2015, A2 Location in patent: Paragraph 00461

8
[ 177906-46-6 ]
[ 22509-74-6 ]
[ 25577-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate 2: potassium hydrogensulfate; sulfuric acid

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/116755, 2015, A2

9
[ 177906-46-6 ]
[ 98-58-8 ]
4-bromo-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation 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].

Reference： [1]Current Patent Assignee: IP GROUP PLC - WO2016/97001, 2016, A1 Location in patent: Page/Page column 48

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 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: IP GROUP PLC - WO2016/97001, 2016, A1

11
[ 177906-46-6 ]
4'-cyano-2-fluoro-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: IP GROUP PLC - WO2016/97001, 2016, A1

12
[ 177906-46-6 ]
2',4',5'-trifluoro-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: IP GROUP PLC - WO2016/97001, 2016, A1

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 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: IP GROUP PLC - WO2016/97001, 2016, A1 Location in patent: Page/Page column 49

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 ]

Yield	Reaction Conditions	Operation 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+).

Reference： [1]Current Patent Assignee: CELLCENTRIC LIMITED - WO2018/73586, 2018, A1 Location in patent: Page/Page column 107

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 ]

Yield	Reaction Conditions	Operation 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) +.

Reference： [1]Current Patent Assignee: BEIGENE LTD. - WO2019/196803, 2019, A1 Location in patent: Paragraph 0352

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 ]

Yield	Reaction Conditions	Operation 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) +.

Reference： [1]Current Patent Assignee: BEIGENE LTD. - WO2019/196803, 2019, A1 Location in patent: Paragraph 0354

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 ]

Yield	Reaction Conditions	Operation 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) +.

Reference： [1]Current Patent Assignee: BEIGENE LTD. - WO2019/196803, 2019, A1 Location in patent: Paragraph 0498

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 ]

Yield	Reaction Conditions	Operation 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) +.

Reference： [1]Current Patent Assignee: BEIGENE LTD. - WO2019/196803, 2019, A1 Location in patent: Paragraph 0668

19
[ 177906-46-6 ]
[ 51940-64-8 ]
ethyl 2-chloro-4-(((1s,4s)-4-hydroxy-4-methylcyclohexyl)amino)pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: WO2019/238929,2019,A1 .Location in patent: Page/Page column 39; 64; 65

20
[ 177906-46-6 ]
2-chloro-4-(((1s,4s)-4-hydroxy-4-methylcyclohexyl)amino)pyrimidine-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC; CANCER RESEARCH UK - WO2019/238929, 2019, A1

21
[ 177906-46-6 ]
2-chloro-9-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-7,9-dihydro-8H-purin-8-one [ No CAS ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC; CANCER RESEARCH UK - WO2019/238929, 2019, A1

22
[ 177906-46-6 ]
2-chloro-9-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-7-methyl-7,9-dihydro-8H-purin-8-one [ No CAS ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC; CANCER RESEARCH UK - WO2019/238929, 2019, A1

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 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC; CANCER RESEARCH UK - WO2019/238929, 2019, A1

24
[ 66336-42-3 ]
[ 177906-46-6 ]
[ 177908-37-1 ]

Reference： [1]Advanced synthesis and catalysis,2020
[2]Advanced synthesis and catalysis,2020

25
C₇H₁₃NO₂ [ No CAS ]
[ 177906-46-6 ]
[ 177908-37-1 ]

Reference： [1]Advanced synthesis and catalysis,2020

26
[ 4746-97-8 ]
[ 177906-46-6 ]
[ 177908-37-1 ]

Reference： [1]Advanced synthesis and catalysis,2020
[2]Advanced synthesis and catalysis,2020

27
[ 17429-02-6 ]
[ 177906-46-6 ]
[ 177908-37-1 ]

Reference： [1]Advanced synthesis and catalysis,2020
[2]Advanced synthesis and catalysis,2020

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 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2020/180959, 2020, A1 Location in patent: Page/Page column 243

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 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: KINNATE BIOPHARMA INC - WO2021/81375, 2021, A1 Location in patent: Paragraph 00313-00315

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 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: KINNATE BIOPHARMA INC - WO2021/81375, 2021, A1

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 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2021/207186, 2021, A1 Location in patent: Page/Page column 150-151

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 ]

Yield	Reaction Conditions	Operation 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;

Reference： [1]Mata, Guillaume; Miles, Dillon H.; Drew, Samuel L.; Fournier, Jeremy; Lawson, Kenneth V.; Mailyan, Artur K.; Sharif, Ehesan U.; Yan, Xuelei; Beatty, Joel W.; Banuelos, Jesus; Chen, Jie; Ginn, Elaine; Chen, Ada; Gerrick, Kimberline Y.; Pham, Amber T.; Wong, Kent; Soni, Divyank; Dhanota, Puja; Shaqfeh, Stefan G.; Meleza, Cesar; Narasappa, Nell; Singh, Hema; Zhao, Xiaoning; Jin, Lixia; Schindler, Ulrike; Walters, Matthew J.; Young, Stephen W.; Walker, Nigel P.; Leleti, Manmohan Reddy; Powers, Jay P.; Jeffrey, Jenna L. [Journal of Medicinal Chemistry, 2022, vol. 65, # 2, p. 1418 - 1444]

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 ]

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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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P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 177906-46-6 ]

Quality Control of [ 177906-46-6 ]

Related Doc. of [ 177906-46-6 ]

Product Details of [ 177906-46-6 ]

Safety of [ 177906-46-6 ]

Application In Synthesis of [ 177906-46-6 ]

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

Related Functional Groups of [ 177906-46-6 ]

Aliphatic Cyclic Hydrocarbons

Alcohols

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 177906-46-6 ]