Methylamine → HCID 69480197, compound

HRID 2364470Notes

Reaction equation

HRID 2364470 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:34])=[C:14]([C:29]([O:31]CC)=O)[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:35][NH2:36]>>[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:34])=[C:14]([C:29]([NH:36][CH3:35])=[O:31])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 69482189HCID 69482189, compound

Product 1

HCID 69480197HCID 69480197, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and methylamine (8 M in ethanol) employing methods similar to those described in Example 202 and was obtained as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.04 (m, 1 H), 8.55 (s, 1 H), 7.41 (s, 1 H), 7.17 (dd, J=8.5, 5.3 Hz, 2 H), 7.02 (t, J=8.6 Hz, 2 H), 4.16-4.11 (m, 4 H), 3.41-3.37 (m, 4 H), 3.01 (d, J=4.9 Hz, 3 H), 2.39 (t, J=8.0 Hz, 2 H), 2.05 (m, 2 H), 1.83 (m, 2 H); HRMS C24H25FN4O4 (M+H)+ calcd 453.1938, found 453.1945.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-4d00b4f353ac45ebaa779c8487c34b2c
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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