Potassium Hydroxide → N-(4-(4-(1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide

HRID 645682Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:31]=[CH:30][N:29](S(C5C=CC(C)=CC=5)(=O)=O)[C:13]=4[N:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]([CH3:28])[C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=4)[N:16]=3)[CH:8]=2)[CH:3]=[N:2]1.[OH-].[K+]>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:31]=[CH:30][NH:29][C:13]=4[N:14]=[C:15]([NH:17][C:18]4[CH:19]=[CH:20][C:21]([N:24]([CH3:28])[C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=4)[N:16]=3)[CH:8]=2)[CH:3]=[N:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(4-(4-(1H-indazol-6-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide (45 mg, 0.080 mmol) in methanol (MeOH) (3 mL), aq. 1N potassium hydroxide (KOH) (0.50 mL, 0.50 mmol) was added. The mixture was then heated at 60° C. for 4 h before it was concentrated in vacuo. The residue was then acidified with acetic acid (HOAc) (0.5 mL) before being purified by HPLC to give the title compound (20 mg). MS 413.1 (M+H) (Compound 6-1).

Workup

concentrationwas concentrated in vacuo
custombefore being purified by HPLC

Sources & evidence

ORD record: ord-9812a8864aa847be81e2287d3500de3a
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Reaction notes

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