Water → HCID 86704233, compound

HRID 624086Notes

Reaction equation

HRID 624086 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([NH:19][C:20]([C:22]3[N:23]=[CH:24][O:25][C:26]=3[C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)=[O:21])[CH:16]=[N:15]2)[N:4]=1.[H-].[Na+].Br[CH2:37][CH3:38].O>CN(C=O)C>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([N:11]([CH2:37][CH3:38])[CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([NH:19][C:20]([C:22]3[N:23]=[CH:24][O:25][C:26]=3[C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)=[O:21])[CH:16]=[N:15]2)[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 60161973HCID 60161973, compound

Product 1

HCID 86704233HCID 86704233, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of N-(1-(2-((4,6-dimethoxypyrimidin-2-yl)amino)ethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide (80 mg, 0.178 mmol) in DMF (1 mL) was added NaH (12 mg, 0.27 mmol). The icebath was removed and the mixture was stirred for 40 min at rt, then 1-bromo ethane (20 uL, 0.25 mmol) was added and stirred for 18 h at rt. To the reaction mixture was added few drops of water and directly purified by prep. HPLC. LC-MS conditions D: tR=1.19 min, [M+H]+=478.3

Workup

  1. customThe icebath was removed
  2. stirringstirred for 18 h at rt
  3. customdirectly purified by prep

Sources & evidence

ORD record
ord-edc05aa592254af8a16086c2d70369c7
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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