4-(1-Pyrrolidinyl)piperidine → HCID 24853125, compound

HRID 659348Notes

Reaction equation

HRID 659348 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.[N:30]1([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:34][CH2:33][CH2:32][CH2:31]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:17]=[CH:18][C:19]([C:20]([N:38]4[CH2:39][CH2:40][CH:35]([N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[CH2:36][CH2:37]4)=[O:21])=[CH:23][CH:24]=3)=[CH:15][C:6]1=2

Participants

3

Reactant 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 24853017HCID 24853017, compound

Product 1

HCID 24853125HCID 24853125, compoundYield 30%

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 4-(1 pyrrolidinyl)piperidine as in General Procedure 8 to give the title compound as a pale yellow solid (30% yield). M.p. 186° C. (dec) m/z=532.30 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.44-1.58 (m, 4H), 1.90-2.06 (m, 2H), 2.28-2.32 (m, 1H), 2.52-2.64 (m, 4H), 2.85-3.11 (m, 3H), 3.70-3.82 (m, 2H), 4.34 (s, 2H), 4.50-4.62 (m, 2H), 5.06 (s, 1H), 5.22 (s, 2H), 6.6.88-6.96 (m, 2H), 7.10-7.22 (m, 1H), 7.20 (s, 1H), 7.40 (dd, J=8.3 Hz, 2H), 8.01 (s, 1H).

Sources & evidence

ORD record
ord-1fa4685f1e074c60ab85a635c66b4672
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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