1-Pyrrolidineethanamine → HCID 24853123, compound

HRID 2074567Notes

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.[NH2:30][CH2:31][CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]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]([NH:30][CH2:31][CH2:32][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)=[O:21])=[CH:18][CH:17]=3)=[CH:15][C:6]1=2

Participants

Reactant 2

HCID 13441-Pyrrolidineethanamine

HCID 24853017HCID 24853017, compound

Product 1

HCID 24853123HCID 24853123, compoundYield 25%

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 N-(2-aminoethyl)pyrrolidine as in General Procedure 8 to give the title compound as a white solid (25% yield). M.p. 235° C. (dec), LCMS: m/z=492.20 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.81-18.5 (m, 4H), 2.55-2.65 (m, 4H), 2.72-2.80 (m, 2H), 3.58-3.62 (m, 2H), 4.68 (s, 2H), 4.99 (s, 1H), 5.23 (s, 2H), 6.85-6.95 (m, 2H), 7.02-7.08 (m, 1H), 7.07 (s, 1H), 7.44 (d, J=8.3 Hz, 2H), 7.83 (d, J=8.1 Hz, 2H), 8.03 (s, 1H), 8.08 (s, 1H).

Sources & evidence

ORD record: ord-1d2689f08f7941d98dbe89f1617ff664
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919502B2

Reaction notes

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