Potassium Hydroxide → HCID 44247564, compound

HRID 2381601Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:10]3[CH:33]=[CH:32][N:31](S(C4C=CC(C)=CC=4)(=O)=O)[C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:14]=2)[CH2:5][CH2:4]1.[OH-].[K+]>CO>[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:10]3[CH:33]=[CH:32][NH:31][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:20][CH:21]=3)[N:14]=2)[CH2:5][CH2:4]1.[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:10]3[CH:33]=[CH:32][NH:31][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:23][CH2:24][N:25]([C:28](=[O:30])[CH3:29])[CH2:26][CH2:27]4)=[CH:20][CH:21]=3)[N:14]=2)[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(4-(4-(4-(4-(aminomethyl)piperidin-1-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (60 mg, 0.10 mmol) in MeOH (3 mL), aq. 1N KOH (1 mL) was added. It was stirred at 60° C. for 3 h. After being concentrated in vacuo, the residue was acidified with HOAc (1 mL). The mixture was then purified by HPLC to give 4-(4-(aminomethyl)piperidin-1-yl)-N-(4-(piperazin-1-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (3 mg) (MS 407.5 (M+H); UV 202.6, 269.9 nm) and 1-(4-(4-(4-(4-(aminomethyl)piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (15 mg) (MS 449.5 (M+H); UV 202.6, 273.4 nm).

Workup

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

Sources & evidence

ORD record: ord-3c811f588f7b4b3090c1f56b21d1b624
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258144B2

Reaction notes

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