Methylamine → HCID 69482771, compound

HRID 2364541Notes

Reaction equation

HRID 2364541 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:35])=[C:14]([C:30]([O:32]CC)=O)[C:15](=[O:29])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:28])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:36][NH2:37]>>[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:35])=[C:14]([C:30]([NH:37][CH3:36])=[O:32])[C:15](=[O:29])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:28])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 69480472HCID 69480472, compound

Product 1

HCID 69482771HCID 69482771, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxo-1-piperidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and methylamine using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.65-1.81 (m, 6 H), 2.19 (t, J=6.21 Hz, 2 H), 2.91 (d, J=4.84 Hz, 3 H), 3.20 (t, J=5.79 Hz, 2 H), 3.38 (q, J=7.09 Hz, 2 H), 4.16-4.25 (m, 4 H), 7.11-7.18 (m, 2 H), 7.37-7.44 (m, 2 H), 8.01 (s, 1 H), 8.55 (d, J=1.68 Hz, 1 H), 10.14 (d, J=4.63 Hz, 1 H), 17.23 (s, 1 H); ES+ MS: 467 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-f090b25e4c5443a2bb59f67244de038b
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…