1-(3-Aminopropyl)-2-pyrrolidinone → HCID 69482446, compound

HRID 2364318Notes

Reaction equation

HRID 2364318 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31](OCC)=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:37][CH2:38][CH2:39][CH2:40][N:41]1[CH2:45][CH2:44][CH2:43][C:42]1=[O:46]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31]([NH:37][CH2:38][CH2:39][CH2:40][N:41]4[CH2:45][CH2:44][CH2:43][C:42]4=[O:46])=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][C:20]3[CH:21]=[CH:22][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][CH:25]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 58882966HCID 58882966, compound

Product 1

HCID 69482446HCID 69482446, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-{[4-(methylsulfonyl)phenyl]methyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 1-(3-aminopropyl)-2-pyrrolidinone employing methods similar to those described in Example 202 and was obtained as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.25 (t, J=5.3 Hz, 1 H), 8.57 (s, 1 H), 7.84 (d, J=8.2 Hz, 2 H), 7.20 (d, J=8.1 Hz, 2 H), 7.02-6.97 (m, 5 H), 5.45 (br, 2 H), 4.02 (s, 2 H), 3.50-3.38 (m, 6 H), 3.03 (s, 3 H), 2.39 (t, J=7.9 Hz, 2 H), 2.04 (m, 2 H), 1.88 (m, 2 H); HRMS C31H31FN4O6S (M+H)+ calcd 607.1948, found 607.2043.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-24340ece295545d38758051165d9ffdc
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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