Dimethylformamide → HCID 69482099, compound

HRID 2364424Notes

Reaction equation

HRID 2364424 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:24])[C:5]1=[O:34].C(N(C(C)C)CC)(C)C.[CH3:44][N:45]([CH:47]=[O:48])[CH3:46]>>[CH3:44][N:45]([CH3:46])[C:47]([NH:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)=[O:24])[C:5]1=[O:34])=[O:48]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 69482180HCID 69482180, compound

Product 1

HCID 69482099HCID 69482099, compound

Procedure

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.025 g, 0.057 mmol) and diisopropyl ethylamine (0.05 mL, 0.29 mmol) in DMF (3 mL) under nitrogen was treated with N,N-dimethyl carbonyl chloride (0.0055 mL, 0.06 mmol) (40° C. After 2½ h the reaction was cooled, concentrated in vacuo, and the resulting residue was triturated with EtOAc and water, filtered, and dried in vacuo to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.84 (s, 1 H), 2.39-2.47 (m, 4 H), 2.52-2.57 (m, 2 H), 2.71 (s, 6 H), 3.23-3.31 (m, 2 H), 3.44-3.55 (m, 2 H), 3.56-3.62 (m, 4 H), 4.12 (s, 2 H), 4.25 (t, J=6.32 Hz, 2 H), 6.57 (t, J=5.55 Hz, 1 H), 7.09-7.18 (m, 2 H), 7.41 (dd, J=8.70, 5.62 Hz, 2 H), 8.30 (s, 1 H), 8.53 (s, 1 H), 10.40 (t, J=5.90 Hz, 1 H); ES+ MS: 541 (M+H+).

Workup

  1. temperatureAfter 2½ h the reaction was cooled
  2. concentrationconcentrated in vacuo
  3. customthe resulting residue was triturated with EtOAc and water
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f39128fd6abd49308a8fe8e811230247
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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