Water → HCID 58930947, compound

HRID 1433702Notes

Reaction equation

HRID 1433702 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 brine, 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 brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37303dff2a894c27898ad7bcf53f8fee
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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