1-Methylpiperazine → 4-Methyl-5-[4-(4-methyl-piperazin-1-YL)-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-1H-pyrrole-2-carboxylic acid (2-morpholin-4-YL-ethyl)-amide

HRID 397389Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]([CH:18]=[C:19]3[C:27]4[C:26](Cl)=[N:25][CH:24]=[N:23][C:22]=4[NH:21][C:20]3=[O:29])=[C:15]([CH3:17])[CH:16]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>>[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]([CH:18]=[C:19]3[C:27]4[C:26]([N:34]5[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]5)=[N:25][CH:24]=[N:23][C:22]=4[NH:21][C:20]3=[O:29])=[C:15]([CH3:17])[CH:16]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 531671-Methylpiperazine

HCID 865864995-(4-chloro-6-oxo-6,7-dihydro-pyrrolo[2,3-d]pyrimidin-5-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)amide

Product 1

HCID 853266454-Methyl-5-[4-(4-methyl-piperazin-1-YL)-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-1H-pyrrole-2-carboxylic acid (2-morpholin-4-YL-ethyl)-amideYield 47%

Procedure

The title compound (47% yield) was prepared from 5-(4-chloro-6-oxo-6,7-dihydro-pyrrolo[2,3-d]pyrimidin-5-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide and 1-methylpiperazine according to the procedure described for Example 14. 1H NMR (300 MHz, DMSO-d6) δ 13.37 (br s, 1H, NH), 11.83 (br s, 1H, NH), 10.56 (v br s, 1H), 8.45 (v br s, 1H), 8.38 (s, 1H, H-vinyl), 7.09 (s, 1H), 6.87 (s, 1H), 3.4-3.6 (m, 10H, 5×CH2), 2.85 (m, 4H, 2×CH2), 2.4-2.6 (m, 6H, 3×CH2), 2.49 (under DMSO, 3H, CH3), 2.31 (s, 3H, CH3). MS 481.3 [M++1].

Sources & evidence

ORD record: ord-7653b492e4b3409d91c169aa045f99a8
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610688B2

Reaction notes

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