1-(3-Aminopropyl)-2-pyrrolidinone → HCID 69480456, compound

HRID 2364564Notes

Reaction equation

HRID 2364564 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][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[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:3]=[CH:4][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][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 69481817HCID 69481817, compound

Product 1

HCID 69480456HCID 69480456, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 1-(3-aminopropyl)-2-pyrrolidinone using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.54 (d, J=3.58 Hz, 4 H), 1.59-1.65 (m, 2 H), 1.65-1.81 (m, 4 H), 1.84-1.97 (m, 2 H), 2.21 (t, J=8.21 Hz, 2 H), 2.35-2.47 (m, 2 H), 3.24 (t, J=6.74 Hz, 2 H), 3.35 (td, J=7.05, 2.95 Hz, 8 H), 4.15-4.25 (m, 4 H), 7.14 (t, J=8.95 Hz, 2 H), 7.31-7.54 (m, 2 H), 8.00 (s, 1 H), 8.56 (d, J=1.47 Hz, 1 H), 10.31 (t, J=5.90 Hz, 1 H), 17.15 (s, 1 H); ES+ MS: 592 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-7f70d66de4bd4559a9ee28c28e206967
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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