1-(3-Aminopropyl)-2-pyrrolidinone → HCID 69482016, compound

HRID 2364290Notes

Reaction equation

HRID 2364290 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:32])=[C:14]([C:27](OCC)=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:33][CH2:34][CH2:35][CH2:36][N:37]1[CH2:41][CH2:40][CH2:39][C:38]1=[O:42]>>[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:32])=[C:14]([C:27]([NH:33][CH2:34][CH2:35][CH2:36][N:37]4[CH2:41][CH2:40][CH2:39][C:38]4=[O:42])=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 69480155HCID 69480155, compound

Product 1

HCID 69482016HCID 69482016, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylsulfonyl)propyl]-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 10.23 (t, J=5.5 Hz, 1 H), 8.55 (s, 1 H), 7.65 (s, 1 H), 7.20 (dd, J=8.5, 5.4 Hz, 2 H), 7.00 (t, J=8.8 Hz, 2 H), 4.39 (t, J=7.7 Hz, 2 H), 4.11 (s, 2 H), 3.46-3.35 (m, 6 H), 3.13 (t, J=7.1 Hz, 2 H), 2.94 (s, 3 H), 2.39 (t, J=8.2 Hz, 2 H), 2.19 (m, 2 H), 2.03 (m, 2 H), 1.85 (m, 2 H); HRMS C27H31FN4O6S (M+H)+ calcd 559.1948, found 559.2055.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-a1af51fcd36642efa001a06214bd9752
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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