4-(1-Pyrrolidinyl)piperidine → HCID 24853226, compound

HRID 659352Notes

Reaction equation

HRID 659352 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]([OH:21])=O)=[CH:17][CH:16]=3)=[CH:14][C:6]1=2.[N:29]1([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:33][CH2:32][CH2:31][CH2:30]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:37]4[CH2:38][CH2:39][CH:34]([N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[CH2:35][CH2:36]4)=[O:21])=[CH:17][CH:16]=3)=[CH:14][C:6]1=2

Participants

3

Reactant 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 24853224HCID 24853224, compound

Product 1

HCID 24853226HCID 24853226, compoundYield 47%

Procedure

4-[1-(2,5-Difluorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]benzoic acid (34 mg) was reacted with 4-(1 pyrrolidinyl)piperidine as in General Procedure 8 to give the title compound as a pale yellow solid (47% yield). M.p. 202-204° C., LCMS: m/z=518.10 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.55-1.58 (m, 2H), 1.77-1.84 (m, 4H), 1.88-2.02 (m, 2H), 2.2402.30 (m, 1H), 2.56-2.62 (M, 4H), 2.90-3.12 (m, 2H), 3.44-3.48 (m, 2H), 3.64-3.68 (m, 2H), 3.77-3.87 (m, 1H), 4.49 (s, 2H), 4.55-4.63 (m, 1H), 4.95 (bs, 1H), 6.76 (s, 1H), 6.93-7.09 (m, 3H), 7.39 (dd, J=8.3 Hz, 4H), 7.72 (s, 1H), 8.08 (s, 1H).

Sources & evidence

ORD record
ord-bd990ed54f5743119fb6e5187d3bf980
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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