3-amino-2-methylpropan-1-ol → HCID 69482445, compound

HRID 2364518Notes

Reaction equation

HRID 2364518 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][CH:37]([CH3:40])[CH2:38][OH: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][CH:37]([CH3:40])[CH2:38][OH: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 101976253-amino-2-methylpropan-1-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 69482445HCID 69482445, 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-2-methyl-1-propanol using methods similar to Example 563 to provide an orange solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.89 (d, J=6.95 Hz, 3 H), 1.52-1.65 (m, 4 H), 1.79-1.88 (m, 1 H), 2.03 (t, J=6.00 Hz, 2 H), 3.20-3.47 (m, 6 H), 3.51 (t, J=6.00 Hz, 2 H), 4.16 (s, 2 H), 4.40 (t, J=6.11 Hz, 2 H), 4.64 (s, 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=1.47 Hz, 1 H), 10.38 (t, J=5.90 Hz, 1 H), 17.24 (s, 1 H); ES+ MS: 511 (M+H+).

Workup

  1. customto provide an orange solid

Sources & evidence

ORD record
ord-167236d3e42d4b6f9729fce1cf8a5d4a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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