2-Butanol, 4-amino- → HCID 69482547, compound

HRID 2364562Notes

Reaction equation

HRID 2364562 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:36])=[C:14]([C:31](OCC)=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:37][CH2:38][CH2:39][CH:40]([OH:42])[CH3:41]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31]([NH:37][CH2:38][CH2:39][CH:40]([OH:42])[CH3:41])=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1702542-Butanol, 4-amino-HCID 69481817HCID 69481817, compound

Product 1

HCID 69482547HCID 69482547, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 4-amino-2-butanol 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), 1.37-1.87 (m, 10 H), 2.36-2.45 (m, 2 H), 3.32-3.48 (m, 5 H), 3.63-3.77 (m, 2 H), 4.12-4.23 (m, 4 H), 4.62 (br. s., 1 H), 7.14 (ddd, J=9.05, 6.63, 2.21 Hz, 2 H), 7.37-7.44 (m, 2 H), 7.99 (d, J=1.05 Hz, 1 H), 8.56 (d, J=1.26 Hz, 1 H), 10.35 (t, J=5.69 Hz, 1 H), 17.26 (s, 1 H); ES+ MS: 539 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-1ff8b1dc0e2e4cf98cc3ad8e0b1e2252
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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