(2R)-1-aminopropan-2-ol → HCID 69480945, compound

HRID 2364542Notes

Reaction equation

HRID 2364542 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](OCC)=[O:31])[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.[NH2:36][CH2:37][C@H:38]([OH:40])[CH3:39]>>[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:36][CH2:37][C@H:38]([OH:40])[CH3:39])=[O:31])[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 439938(2R)-1-aminopropan-2-olHCID 69480472HCID 69480472, compound

Product 1

HCID 69480945HCID 69480945, 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 (2R)-1-amino-2-propanol using methods similar to Example 563 to provide a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.09 (t, J=6.63 Hz, 3 H), 1.66-1.80 (m, 6 H), 2.19 (t, J=5.79 Hz, 2 H), 3.16-3.25 (m, 4 H), 3.34-3.48 (m, 2 H), 3.73-3.87 (m, 1 H), 4.17-4.24 (m, 4 H), 4.96 (d, J=4.63 Hz, 1 H), 7.11-7.17 (m, 2 H), 7.38-7.43 (m, 2 H), 8.00 (s, 1 H), 8.56 (s, 1 H), 10.43 (s, 1 H), 16.84 (s, 1 H); ES+ MS: 511 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-ad722d5efea74f07b502a48690434fe5
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…