Dimethylformamide → HCID 69482241, compound

HRID 2364414Notes

Reaction equation

HRID 2364414 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][O:28][CH2:29][CH2:30][OH:31])=[O:24])[C:5]1=[O:32].C(N(C(C)C)CC)(C)C.[CH3:42][N:43]([CH:45]=[O:46])[CH3:44]>>[CH3:42][N:43]([CH3:44])[C:45]([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][O:28][CH2:29][CH2:30][OH:31])=[O:24])[C:5]1=[O:32])=[O:46]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 69482715HCID 69482715, compound

Product 1

HCID 69482241HCID 69482241, compound

Procedure

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(2-hydroxyethyl)oxy]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 treated with 1N NaHSO4, filtered, washed with water, and dried in vacuo to provide the title compound as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.73 (s, 1 H), 2.70 (s, 6 H), 3.24-3.30 (m, 3 H), 3.46-3.62 (m, 7 H), 4.12 (s, 2 H), 4.25 (t, J=6.32 Hz, 2 H), 4.62 (t, J=5.19 Hz, 1 H), 6.56 (t, J=5.76 Hz, 1 H), 7.10-7.18 (m, 2 H), 7.37-7.44 (m, 2 H), 8.30 (s, 1 H), 8.53 (d, J=1.69 Hz, 1 H), 10.41 (t, J=5.26 Hz, 1 H); ES+ MS: 516 (M+H+).

Workup

  1. temperatureAfter 2½ h the reaction was cooled
  2. concentrationconcentrated in vacuo
  3. additionthe resulting residue treated with 1N NaHSO4
  4. filtrationfiltered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-18c8a5139f9649e1ba8c0364122d6712
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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