Sodium Hydroxide → 1,1-dimethylethyl 4-(5-{4-[3-(4-aminophenyl)-1-methyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-2-pyrimidinyl)-1-piperazinecarboxylate

HRID 1821313Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[N:19](S(C5C=CC=CC=5)(=O)=O)[C:20]([C:22]5[CH:23]=[N:24][C:25]([N:28]6[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]6)=[N:26][CH:27]=5)=[CH:21][C:14]=34)=[CH:11][N:10]([CH3:50])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[NH:19][C:20]([C:22]5[CH:27]=[N:26][C:25]([N:28]6[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:32][CH2:33]6)=[N:24][CH:23]=5)=[CH:21][C:14]=34)=[CH:11][N:10]([CH3:50])[N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1,1-dimethylethyl 4-{5-[4-[3-(4-aminophenyl)-1-methyl-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-pyrimidinyl}-1-piperazinecarboxylate (0.333 mmol) in methanol (20 ml) was added 6M NaOH(aq) (1.5 ml). The resulting solution was heated at 70° C. for 4 hours, concentrated in vacuo and the yellow residue taken up in chloroform. After washing with saturated NH4Cl(aq), the organic layer was dried (MgSO4), filtered and concentrated to yield the title product (99%) as a yellow solid which was used crude in the next step. ESMS [M+H]+: 552.2.

Workup

concentrationconcentrated in vacuo
washAfter washing with saturated NH4Cl(aq)
dry with materialthe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-09b2582db5b742a5836b87e0fd136a3f
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605266B2

Reaction notes

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