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

HRID 2281503Notes

Reaction equation

C(CC([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[C:14]3[CH:31]=[CH:30][N:29](S(C4C=CC(C)=CC=4)(=O)=O)[C:15]=3[N:16]=[C:17]([NH:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][CH:21]=3)[N:18]=2)[CH2:8][CH2:7]1)=O)#N.[OH-].[K+]>O1CCOCC1.CO>[NH:6]1[CH2:7][CH2:8][CH:9]([NH:12][C:13]2[C:14]3[CH:31]=[CH:30][NH:29][C:15]=3[N:16]=[C:17]([NH:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][CH:21]=3)[N:18]=2)[CH2:10][CH2:11]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-(4-(1-(2-cyanoacetyl)piperidin-4-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (45 mg, 0.078 mmol) in dioxane (2 mL) and MeOH (1 mL), aq. 1N KOH (1.0 mL, 1.0 mmol) was added. The mixture was stirred at 70° C. for 4 h. It was concentrated in vacuo. The residue was acidified with HOAc (1 mL) before being purified by HPLC to give 4-(4-(piperidin-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (20 mg).

Workup

concentrationIt was concentrated in vacuo
custombefore being purified by HPLC

Sources & evidence

ORD record: ord-9ad4dd8916f64c49bf1c2b2edcf88e2c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139581B2

Reaction notes

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