Acetic Acid → HCID 178494225, compound

HRID 1487590Notes

Reaction equation

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

Participants

Reactant 2

HCID 176Acetic Acid

HCID 86726425HCID 86726425, compound

Product 1

HCID 178494225HCID 178494225, compoundYield 73%

Conditions

Temperature: 115 °C

Procedure

3-Chloro-4-(5-(3,4-diaminophenyl)-4-methoxy-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-N,N-dimethylbenzamide (1 equiv) was dissolved in acetic acid (40 equiv) and stirred at 115° C. for 3 h. After the reaction was complete, the solvent was removed under high vacuum. The residue was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to afford the title compound (73% yield). MS (ESI) m/z 606.2[M+1]+.

Workup

customthe solvent was removed under high vacuum
customThe residue was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-76d9cd16d675445eb2dbe54a70c4f895
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428509B2

Reaction notes

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