1-Butanol → HCID 86628039, compound

HRID 645700Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[C:12]4C=CN(S(C5C=CC(C)=CC=5)(=O)=O)[C:13]=4[N:14]=[C:15](Cl)[N:16]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.NC1C=CC([N:38]2[CH2:43][CH2:42][CH:41]([C:44]([N:46]([CH3:48])[CH3:47])=[O:45])[CH2:40][CH2:39]2)=CC=1.C[Si](Cl)(C)C.[OH-].[K+].[CH2:56](O)[CH2:57][CH2:58][CH3:59]>CO.O>[NH:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[CH:9]=[CH:4][C:5]([C:41]4([C:44]([N:46]([CH3:47])[CH3:48])=[O:45])[CH2:40][CH2:39][NH:38][CH2:43][CH2:42]4)=[C:13]([NH:14][C:15]4[N:16]=[CH:59][C:58]5[CH:57]=[CH:56][NH:3][C:2]=5[N:1]=4)[CH:12]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 115 °C

Procedure

To a mixture of N-(1H-benzo[d]imidazol-6-yl)-2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.1 g, 0.24 mmol) in n-butyl alcohol (1 mL) was added 1-(4-aminophenyl)-N,N-dimethylpiperidine-4-carboxamide (0.11 g, 0.44 mmol) and TMSCl (0.014 mL, 0.11 mmol). After heating at 115° C. for 15 h, the mixture was diluted with MeOH (1 mL), and a solution of KOH (0.1 g) in H2O (0.5 mL) was added. After heating at 60° C. for 2 h, the mixture was purified by preparative HPLC to give 1-(4-(4-(1H-benzo[d]imidazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylaminophenyl)-N,N-dimethylpiperidine-4-carboxamide (0.02 g, MS (MH 496.3) (Compound 18-1).

Workup

temperatureAfter heating at 60° C. for 2 h
customthe mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-d44d437431a94f6fb1ed5675656bcac0
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Reaction notes

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