HCID 24729719, compound → HCID 69482650, compound

HRID 2364519Notes

Reaction equation

HRID 2364519 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][CH:36]([CH:40]1[CH2:42][CH2:41]1)[CH2:37][CH2:38][OH:39]>>[CH:40]1([CH:36]([NH:35][C:29]([C:14]2[C:15](=[O:28])[N:16]([CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3=[O:27])[C:17]3[C:12]([C:13]=2[OH:34])=[N:11][CH:10]=[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:18]=3)=[O:30])[CH2:37][CH2:38][OH:39])[CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 24729719HCID 24729719, compoundHCID 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 69482650HCID 69482650, 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 3-amino-3-cyclopropyl-1-propanol using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.24-0.34 (m, 2 H), 0.38-0.46 (m, 1 H), 0.52 (t, J=8.74 Hz, 1 H), 1.00-1.11 (m, 1 H), 1.54-1.67 (m, 4 H), 1.75-1.88 (m, 2 H), 2.04 (s, 2 H), 3.28 (t, J=5.69 Hz, 3 H), 3.46-3.60 (m, 5 H), 4.17 (s, 2 H), 4.41 (t, J=6.95 Hz, 2 H), 7.11-7.17 (m, 2 H), 7.38-7.45 (m, 2 H), 8.22 (s, 1 H), 8.56 (d, J=1.47 Hz, 1 H), 10.36 (d, J=8.63 Hz, 1 H), 17.23 (s, 1 H); ES+ MS: 537 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-f216ad94455043febc71be6e5dde168c
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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