1-Propanol, 3-amino-2,2-dimethyl- → HCID 69480222, compound

HRID 2364251Notes

Reaction equation

HRID 2364251 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:33])=[C:14]([C:28](OCC)=[O:29])[C:15](=[O:27])[N:16]3[CH2:19][C:20](=[O:26])[N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:34][CH2:35][C:36]([CH3:40])([CH3:39])[CH2:37][OH:38]>>[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:33])=[C:14]([C:28]([NH:34][CH2:35][C:36]([CH3:40])([CH3:39])[CH2:37][OH:38])=[O:29])[C:15](=[O:27])[N:16]3[CH2:19][C:20](=[O:26])[N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 58882934HCID 58882934, compound

Product 1

HCID 69480222HCID 69480222, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-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 (CDCl3) δ 14.4 (1H, br), 10.32 (1H, m), 8.56 (1H, s), 7.15 (2H, dd, J=8.6, 5.5 Hz), 7.02 (3H, m), 4.88 (2H, s), 4.12 (2H, s), 3.49 (2H, t, J=7 Hz), 3.46 (2H, t, J=7 Hz), 3.33 (1H, t, J=7 Hz), 3.30 (2H, d, J=7 Hz), 3.24 (2H, d, J=7 Hz), 2.05 (2H, m, J=7 Hz), 1.90 (2H, m, J=7 Hz), 0.94 (6H, s); HRMS calcd for C27H31FN4O5+H+: 511.2357. Found: 511.2341.

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-ccd21a943f934b088653a8e22671c57a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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