N-(3-Aminopropyl)morpholine → HCID 69482833, compound

HRID 2364248Notes

Reaction equation

HRID 2364248 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][S:22]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:37][CH2:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>>[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[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:23])=[O:24])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 69481048HCID 69481048, compound

Product 1

HCID 69482833HCID 69482833, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(1-pyrrolidinylsulfonyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 3-aminopropyl morpholine employing methods similar to those described in Example 202 and was obtained as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.22 (t, J=5.3 Hz, 1 H), 8.57 (s, 1 H), 7.76 (s, 1 H), 7.22 (dd, J=8.5, 5.5 Hz, 2 H), 7.02 (t, J=8.6 Hz, 2 H), 4.39 (t, J=8.0 Hz, 2 H), 4.13 (s, 2 H), 3.84-3.82 (m, 4 H), 3.53 (q, J=6.6 Hz, 2 H), 3.38-3.34 (m, 4 H), 3.06 (t, J=6.5 Hz, 2 H), 2.71-2.62 (m, 6 H), 2.17 (m, 2 H), 1.98-1.93 (m, 6 H); HRMS C30H38FN5O6S (M+H)+ calcd 616.2527, found 616.2609.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-484b6358dfdd44608bd14507a8144f05
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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