Acetic Acid → 4-(4-(1-methyl-1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide

HRID 645715Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[C:13]4[CH:30]=[CH:29][N:28](S(C5C=CC(C)=CC=5)(=O)=O)[C:14]=4[N:15]=[C:16]([NH:18][C:19]4[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=4)[N:17]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[OH-].[K+].CC(O)=O>O1CCOCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[C:13]4[CH:30]=[CH:29][NH:28][C:14]=4[N:15]=[C:16]([NH:18][C:19]4[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=4)[N:17]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-(4-(1-methyl-1H-indazol-5-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (40 mg, 0.072 mmol) in dioxane (2 mL), aq. 1N KOH (1.8 mL, 1.80 mmol) was added. The mixture was stirred at 70° C. for 20 h. HOAc (1.0 mL) was added. The mixture was purified by HPLC to give the titled compound (7 mg). MS 399.2 (M+H) (Compound 25-1).

Workup

customThe mixture was purified by HPLC

Sources & evidence

ORD record: ord-d03daef91127444fb8c40f5ff1a4006b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Reaction notes

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