Chlorotrimethylsilane → 4-(4-(piperidin-4-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide

HRID 2281501Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:21][CH:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]([NH2:42])=[O:41])=[CH:38][CH:37]=1.C[Si](Cl)(C)C>C(O)CCC>[NH:25]1[CH2:24][CH2:23][CH:22]([NH:21][C:4]2[C:5]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=4)(=[O:12])=[O:13])[C:6]=3[N:7]=[C:2]([NH:35][C:36]3[CH:44]=[CH:43][C:39]([C:40]([NH2:42])=[O:41])=[CH:38][CH:37]=3)[N:3]=2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 116 °C

Procedure

A mixture of tert-butyl 4-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (202 mg, 0.400 mmol), 4-aminobenzamide (82 mg, 0.60 mmol) and trimethylsilyl chloride (0.200 mL, 1.58 mmol) in nBuOH (4 mL) was stirred at 116° C. in a sealed tube for 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give 4-(4-(piperidin-4-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (58 mg).

Workup

concentrationIt was concentrated in vacuo
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-045f332346b0499f91656de3a9ab9d63
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139581B2

Reaction notes

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