(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine → HCID 24853225, compound

HRID 659351Notes

Reaction equation

HRID 659351 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=3)=[CH:14][C:6]1=2.[NH:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>>[F:1][C:2]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([N:29]4[CH2:33][CH2:32][CH2:31][C@H:30]4[CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[O:20])=[CH:17][CH:16]=3)=[CH:14][C:6]1=2

Participants

3

Reactant 2

HCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 24853224HCID 24853224, compound

Product 1

HCID 24853225HCID 24853225, compoundYield 53%

Procedure

4-[1-(2,5-Difluorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]benzoic acid (50 mg) was reacted with (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine as in General Procedure 8 to give the title compound as a pale yellow solid (53% yield). M.p. 143-144° C., LCMS: m/z=518.30 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.48-1.58 (m, 1H), 1.87-2.15 (m, 4H), 2.17-2.22 (m, 3H), 2.55-2.64 (m, 4H), 2.83-2.89 (m, 1H), 3.12-3.23 (m, 1H), 3.42-3.50 (m, 2H), 3.60-3.64 (m, 2H), 4.40-4.49 (m, 3H), 5.07 (bs, 1H), 6.76 (s, 1H), 6.86-7.09 (m, 3H), 7.41 (d, J=8.1 Hz, 2H), 7.45-7.52 (m, 2H), 7.73 (s, 1H).

Sources & evidence

ORD record
ord-89e32d7adca14c1e97aecf7c0e8c9f72
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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