Acetic Acid → N4-(1-methyl-1H-indazol-6-yl)-N2-(4-(piperazin-1-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

HRID 645709Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]3[C:13]4[CH:36]=[CH:35][NH:34][C:14]=4[N:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][N:28](C(=O)C)[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[N:17]=3)[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][CH:7]=[C:8]([NH:11][C:12]3[C:13]4[CH:36]=[CH:35][NH:34][C:14]=4[N:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[N:17]=3)[CH:9]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1-(4-(4-(4-(1-methyl-1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (30 mg, 0.047 mmol) in dioxane (2 mL), aq. 1N KOH (2 mL, 2.00 mmol) was added. The mixture was stirred at 70° C. for 3 h. HOAc (0.3 mL) was added. The mixture was purified by HPLC to give N4-(1-methyl-1H-indazol-6-yl)-N2-(4-(piperazin-1-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (3 mg), MS 440.3 (M+H) (Compound 22-1); and 1-(4-(4-(4-(1-methyl-1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (7 mg), MS 482.3 (M+H) (Compound 22-2).

Workup

customThe mixture was purified by HPLC

Sources & evidence

ORD record: ord-100ee9230b164036b299d81dea7a9368
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Reaction notes

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