Potassium Hydroxide → 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-3-carboxamide

HRID 2281373Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[C:19]([N:36]4[CH2:41][CH2:40][CH2:39][CH:38]([C:42]([NH2:44])=[O:43])[CH2:37]4)[C:20]4[CH:25]=[CH:24][N:23](S(C5C=CC(C)=CC=5)(=O)=O)[C:21]=4[N:22]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH-].[K+]>CO>[N:7]1([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[C:19]([N:36]4[CH2:41][CH2:40][CH2:39][CH:38]([C:42]([NH2:44])=[O:43])[CH2:37]4)[C:20]4[CH:25]=[CH:24][NH:23][C:21]=4[N:22]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]1.[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[C:19]([N:36]4[CH2:41][CH2:40][CH2:39][CH:38]([C:42]([NH2:44])=[O:43])[CH2:37]4)[C:20]4[CH:25]=[CH:24][NH:23][C:21]=4[N:22]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-3-carboxamide (12 mg, 0.019 mmol) in MeOH (2 mL), aq. 1N KOH (1 mL) was added. It was stirred at 60° C. for 2 h. After being concentrated in vacuo, the residue was acidified with HOAc (1 mL). The mixture was then purified by HPLC to give 1-(2-(4-(piperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-3-carboxamide (2 mg) (MS 421.5 (M+H)) and 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-3-carboxamide (8 mg) (MS 463.6 (M+H)); UV 202.6, 274.6 nm).

Workup

concentrationAfter being concentrated in vacuo
customThe mixture was then purified by HPLC

Sources & evidence

ORD record: ord-97e296d63e49472c8c86a0a2908cbcaf
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139581B2

Reaction notes

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