2-Methoxyethylamine → (R)-N-(1-(5-bromo-2-((2-methoxyethyl)amino)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

HRID 2170325Notes

Reaction equation

HRID 2170325 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Br:6][C:7]1[C:8]([C@H:17]([NH:27][C:28](=[O:43])[CH2:29][N:30]2[C:38]3[CH2:37][CH2:36][CH2:35][CH2:34][C:33]=3[C:32]([C:39]([F:42])([F:41])[F:40])=[N:31]2)[CH2:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)=[N:9][C:10](S(C)(=O)=O)=[N:11][CH:12]=1>ClCCl>[Br:6][C:7]1[C:8]([C@H:17]([NH:27][C:28](=[O:43])[CH2:29][N:30]2[C:38]3[CH2:37][CH2:36][CH2:35][CH2:34][C:33]=3[C:32]([C:39]([F:42])([F:41])[F:40])=[N:31]2)[CH2:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)=[N:9][C:10]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 90281548(R)-N-(1-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

Product 1

HCID 90281480(R)-N-(1-(5-bromo-2-((2-methoxyethyl)amino)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxyethylamine (0.086 ml, 1 mmol) was added at room temperature to a solution of compound 11H (62 mg, 0.1 mmol) in dichloromethane (5 mL). Stirring was continued at 45° C. for overnight. The solvent was evaporated and the crude product was purified by silica gel chromatography using an ethyl acetate/hexanes eluent to yield the title compound. MS (m/z) 618.00 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6beed32870b04238b4495f457d0cb817
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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