Water → HCID 86732449, compound

HRID 1776421Notes

Reaction equation

HRID 1776421 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[Br:9][C:10]1[CH:40]=[C:39](F)[C:13]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24]3[N:29]=[C:28]([NH:30][C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[C:27]([O:37][CH3:38])=[CH:26][N:25]=3)=[N:16]2)=[C:12]([F:42])[CH:11]=1.O>CN(C=O)C>[Br:9][C:10]1[CH:40]=[C:39]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[C:13]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24]3[N:29]=[C:28]([NH:30][C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[C:27]([O:37][CH3:38])=[CH:26][N:25]=3)=[N:16]2)=[C:12]([F:42])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 71553449HCID 71553449, compound

Product 1

HCID 86732449HCID 86732449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

38.2 mg of 2,2,2-trifluoroethanol (0.382 mmol, 2 eq.) were dissolved in 1.5 ml of dry DMF under nitrogen atmosphere. 16.8 mg of 60% sodium hydrid in paraffin oil (0.42 mmol, 2.2 eq.) were added. The suspension was stirred at room temperature for 15 minutes. 100 mg of 2-[1-(4-bromo-2,6-difluorobenzyl)-1H-indazol-3-yl]-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine (2-12-1, 0.191 mmol, 1 eq.) were added. The reaction mixture was stirred at room temperature for 18 hours. Water was added dropwise. The suspension was filtered off. The precipitate was dried at 50° C. under vacuo. The precipitate was purified by preparative HPLC to yield 34 mg (0.05 mmol, 28%) of the analytically pure target compound.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. filtrationThe suspension was filtered off
  3. customThe precipitate was dried at 50° C. under vacuo
  4. customThe precipitate was purified by preparative HPLC
  5. customto yield 34 mg (0.05 mmol, 28%) of the analytically pure target compound

Sources & evidence

ORD record
ord-76bf6984c45f4fdabf8e5625bbc0bce5
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

Loading…