Water → HCID 58930947, compound

HRID 388041Notes

Reaction equation

HRID 388041 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:32]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:18]3[N:19]=[CH:20][N:21]=[C:22]([O:23][C:24]4[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([F:31])[CH:25]=4)[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:41]1([NH2:44])[CH2:43][CH2:42]1.O.CN(C)[CH:48]=[O:49]>N1C=CC=CC=1.C(Cl)(=O)OC1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:32]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:18]3[N:19]=[CH:20][N:21]=[C:22]([O:23][C:24]4[CH:29]=[CH:28][C:27]([NH:30][C:48]([NH:44][CH:41]5[CH2:43][CH2:42]5)=[O:49])=[C:26]([F:31])[CH:25]=4)[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 58930873HCID 58930873, compound

Product 1

HCID 58930947HCID 58930947, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 15891Phenyl chloroformateSolvent

Procedure

After dissolving 261 mg of 4-[6-(4-benzyloxyphenyl)-7-(trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-2-fluorophenylamine in 3 ml of dimethylformamide, 0.053 ml of pyridine and 0.082 ml of phenyl chlorocarbonate were added, the mixture was stirred at room temperature for 2 hours, 0.081 ml of cyclopropylamine was added and the mixture was further stirred overnight. Water was added, liquid separation and extraction were performed with ethyl acetate, and the organic layer was washed with saturated saline, dried over sodium sulfate, concentrated and subjected to silica gel column chromatography (hexane-ethyl acetate) to obtain 265 mg of the title compound.

Workup

  1. additionwere added
  2. waitthe mixture was further stirred overnight
  3. customliquid separation and extraction
  4. washthe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-64edce4ff7f541f4a7b12c7ca7eea809
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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