2-Amino-2-methyl-1-propanol → HCID 69482153, compound

HRID 2364377Notes

Reaction equation

HRID 2364377 reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29].[NH2:32][C:33]([CH3:37])([CH3:36])[CH2:34][OH:35]>>[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:32][C:33]([CH3:37])([CH3:36])[CH2:34][OH:35])=[O:25])[C:6]1=[O:29]

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 58882926HCID 58882926, compound

Product 1

HCID 69482153HCID 69482153, compound

Procedure

This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-amino-2-methyl-1-propanol employing methods similar to those described in Example 245 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 cream-colored solid: 1H NMR (d6-DMSO) δ 10.35 (1H, s), 8.49 (1H, d, J=1.3 Hz), 7.74 (1H, s), 7.32 (2H, dd, J=8.6, 5.6 Hz), 7.12 (2H, t, J˜9 Hz), 5.11 (2H, s), 5.09 (1H, m), 4.10 (2H, s), 3.44 (2H, d, J=5 Hz), 3.12 (3H, s), 2.82 (3H, s), 1.32 (6H, s); HRMS calcd for C24H27FN4O5+H+: 471.2044. Found: 471.2040.

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 cream-colored solid

Sources & evidence

ORD record
ord-81be3c3fb40e4ab1b1879c0782c06596
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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