Diisopropylethylamine → 1-(4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazin-1-yl)-2-(3-nitrophenyl)ethanone

HRID 1892145Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[C:20]1[C:21]2[C:28]([CH3:29])=[CH:27][NH:26][C:22]=2[N:23]=[CH:24][N:25]=1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[CH3:29][C:28]1[C:21]2[C:20]([N:16]3[CH2:15][CH2:14][N:13]([C:11](=[O:12])[CH2:10][C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[CH2:18][CH2:17]3)=[N:25][CH:24]=[N:23][C:22]=2[NH:26][CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(3-Nitrophenyl)-1-(piperazin-1-yl)ethanone from step A (0.32 g, 0.9 mmol), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.168 g, 1.0 mmol), and diisopropylethylamine (0.1 ml) were combined in isopropanol and heated at 80° C. for 24 hours. The product was isolated by prep HPLC to give 1-(4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazin-1-yl)-2-(3-nitrophenyl)ethanone.

Workup

customThe product was isolated by prep HPLC

Sources & evidence

ORD record: ord-112eb42083e5422088edbd298c4062a7
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507672B2

Reaction notes

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