1-Propanol, 3-amino-2,2-dimethyl- → HCID 69482644, compound

HRID 2364269Notes

Reaction equation

HRID 2364269 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:24])=[C:14]([C:20](OC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1.[NH2:29][CH2:30][C:31]([CH3:35])([CH3:34])[CH2:32][OH:33]>>[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:24])=[C:14]([C:20]([NH:29][CH2:30][C:31]([CH3:35])([CH3:34])[CH2:32][OH:33])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1

Participants

3

Reactant 2

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 69482880HCID 69482880, compound

Product 1

HCID 69482644HCID 69482644, compound

Procedure

This compound was prepared from methyl 7-{[4-fluoro-2-(trifluoromethyl)phenyl]methyl}-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 3-amino-2,2-dimethyl-1-propanol employing methods similar to those those described in Example 9 and was purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.70 (1H, s), 10.37 (1H, t, J=6 Hz), 8.47 (1H, d, J=1.5 Hz), 7.67 (1H, dd, J=9.3, 2.4 Hz), 7.59-7.51 (2H, m), 7.30 (1H, s), 4.72 (1H, t, J=5 Hz), 4.30 (2H, s), 3.23 (2H, d, J=6 Hz), 3.16 (2H, d, J=5 Hz), 0.83 (6H, s); HRMS calcd for C22H21F4N3O4+H+: 468.1546. Found: 468.1558.

Workup

  1. customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)
  2. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-89a9b2ecf30c4661945c03474b4074bd
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…