(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine → 1-[(2,5-Difluorophenyl)methyl]-3,4-dihydro-7-[4-[[(2S)-2-(1-pyrrolidinylmethyl)-1-pyrrolidinyl]carbonyl]phenyl]pyrido[2,3-b]pyrazin-2(1H)-one

HRID 2074566Notes

Reaction equation

HRID 2074566 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[CH2:9][NH:8][C:7]2[N:12]=[CH:13][C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=3)=[CH:15][C:6]1=2.[NH:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[F:1][C:2]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[CH2:9][NH:8][C:7]2[N:12]=[CH:13][C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([N:30]4[CH2:34][CH2:33][CH2:32][C@H:31]4[CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[O:21])=[CH:18][CH:17]=3)=[CH:15][C:6]1=2

Participants

3

Reactant 2

HCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 24853017HCID 24853017, compound

Product 1

HCID 248530181-[(2,5-Difluorophenyl)methyl]-3,4-dihydro-7-[4-[[(2S)-2-(1-pyrrolidinylmethyl)-1-pyrrolidinyl]carbonyl]phenyl]pyrido[2,3-b]pyrazin-2(1H)-oneYield 32%

Procedure

4-[1-(2,5-Difluorobenzyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]benzoic acid (35 mg) was reacted with (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine as in General Procedure 8 to give the title compound as a white solid (32% yield). M.p. 125° C., LCMS: m/z=532.10 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.22-1.26 (m, 2H), 1.68-1.82 (m, 4H), 1.89-2.15 (m, 4H), 2.56-2.70 (m, 3H), 2.80-2.90 (m, 1H), 3.42-3.52 (m, 1H), 4.33 (s, 2H), 4.43-4.50 (m, 1H), 5.02 (bs, 1H), 5.22 (s, 2H), 6.91-6.98 (m, 2H), 7.04-7.10 (m, 1H), 7.21 (d, J=1.5 Hz, 1H), 7.39 (d, J=8.1 Hz, 2H), 7.54 (bd, J=7.6 Hz, 2H), 8.01 (d, J=1.5 Hz, 2H).

Sources & evidence

ORD record
ord-c5a8473b613a43a1a2dfa971d7eada16
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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