2-Butanol, 4-amino- → HCID 69481490, compound

HRID 2364515Notes

Reaction equation

HRID 2364515 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][CH2:37][CH: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:34])=[C:14]([C:29]([NH:35][CH2:36][CH2:37][CH:38]([OH:40])[CH3:39])=[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 1702542-Butanol, 4-amino-HCID 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 69481490HCID 69481490, 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 4-amino-2-butanol using methods similar to Example 563 to provide a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.06-1.12 (m, 3 H), 1.53-1.68 (m, 6 H), 2.04 (t, J=5.90 Hz, 2 H), 3.22-3.30 (m, 2 H), 3.48 (dt, J=13.48, 6.74 Hz, 4 H), 3.62-3.76 (m, 1 H), 4.16 (s, 2 H), 4.39 (t, J=6.21 Hz, 2 H), 4.64 (d, J=4.63 Hz, 1 H), 7.11-7.18 (m, 2 H), 7.38-7.44 (m, 2 H), 8.19 (s, 1 H), 8.56 (d, J=1.26 Hz, 1 H), 10.33 (t, J=5.48 Hz, 1 H), 17.27 (s, 1 H); ES+ MS: 511 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-38b9d1bb38c14690ab8309f3b3546a67
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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