(2R)-1-aminopropan-2-ol → HCID 69480339, compound

HRID 2364507Notes

Reaction equation

HRID 2364507 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](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:35][CH2:36][C@H:37]([OH:39])[CH3:38]>>[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:35][CH2:36][C@H:37]([OH:39])[CH3:38])=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 439938(2R)-1-aminopropan-2-olHCID 69482570Ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69480339HCID 69480339, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (2R)-1-amino-2-propanol using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.10 (d, J=6.32 Hz, 3 H), 1.55-1.65 (m, 4 H), 2.04 (t, J=5.79 Hz, 2 H), 3.15-3.28 (m, 2 H), 3.40-3.53 (m, 4 H), 3.81 (br. s., 1 H), 4.16 (s, 2 H), 4.39 (t, J=6.42 Hz, 2 H), 4.95 (d, J=3.58 Hz, 1 H), 7.11-7.17 (m, 2 H), 7.38-7.43 (m, 2 H), 8.20 (d, J=1.47 Hz, 1 H), 8.56 (d, J=1.68 Hz, 1 H), 10.42 (t, J=5.16 Hz, 1 H), 17.23 (s, 1 H); ES+ MS: 497 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-db6bf9a9ba204f549e514a9d6f81f0e9
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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