Ammonium Chloride → 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

HRID 29007Notes

Reaction equation

[Cl-].[NH4+].[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([S:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)(=[O:39])=[O:38])[C:16]([C:18]4[CH:19]=[N:20][C:21]([N:24]5[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]5)=[N:22][CH:23]=4)=[CH:17][C:10]=23)[C:6]([C:46]2[CH:51]=[CH:50][C:49]([N+:52]([O-])=O)=[CH:48][CH:47]=2)=[N:5]1>O.CO.[Fe]>[NH2:52][C:49]1[CH:50]=[CH:51][C:46]([C:6]2[C:7]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]4[N:15]([S:37]([C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)(=[O:38])=[O:39])[C:16]([C:18]5[CH:23]=[N:22][C:21]([N:24]6[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]6)=[N:20][CH:19]=5)=[CH:17][C:10]=34)=[CH:8][N:4]([CH3:3])[N:5]=2)=[CH:47][CH:48]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of ammonium chloride (3.00 mmol) in H2O (5 ml) was added iron powder (1.66 mmol) followed by a solution of 1,1-dimethylethyl 4-{5-[4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-pyrimidinyl}-1-piperazinecarboxylate (0.333 mmol) in methanol (10 ml). The resulting mixture was heated at 70° C. for 2 hours, the hot solution filtered through a pad of celite 545 and concentrated to yield the title product as a yellow solid (quant.) which was used crude in the next step. ESMS [M+H]+: 692.2.

Workup

filtrationthe hot solution filtered through a pad of celite 545
concentrationconcentrated

Sources & evidence

ORD record: ord-8c847295942b4bd190403a51735d1ba9
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419988B2

Reaction notes

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