Dimethylformamide → HCID 69482240, compound

HRID 2364413Notes

Reaction equation

HRID 2364413 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][CH:27]2[CH2:31][CH2:30][CH2:29][O:28]2)=[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][CH:27]2[CH2:31][CH2:30][CH2:29][O:28]2)=[O:24])[C:5]1=[O:32])=[O:46]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 69480879HCID 69480879, compound

Product 1

HCID 69482240HCID 69482240, compound

Procedure

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(tetrahydro-2-furanylmethyl)-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 an orange solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.98-1.34 (m, 1 H), 1.48-1.67 (m, 1 H), 1.67-2.12 (m, 3 H), 2.70 (s, 6 H), 3.32-3.41 (m, 1 H), 3.57 (d, J=18.81 Hz, 1 H), 3.63-3.71 (m, 1 H), 3.78-3.85 (m, 1 H), 4.00 (d, J=1.97 Hz, 2 H), 4.12 (s, 3 H), 4.26 (t, J=6.04 Hz, 2 H), 6.52-6.57 (m, 1 H), 7.14 (t, J=8.70 Hz, 2 H), 7.35-7.43 (m, 2 H), 8.28 (s, 1 H), 8.53 (s, 1 H), 10.46 (s, 1 H); ES+ MS: 512 (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-172e364573754f1e83603a45327f9dd3
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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