Acetic Anhydride → HCID 69481049, compound

HRID 2364415Notes

Reaction equation

HRID 2364415 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.[C:42](OC(=O)C)(=[O:44])[CH3:43]>CN(C=O)C>[C:42]([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:44])[CH3:43]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 69480879HCID 69480879, compound

Product 1

HCID 69481049HCID 69481049, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 acetic anhydride (0.06 mL, 0.63 mmol) at 40° C. The reaction was concentrated in vacuo and the resulting residue was treated with 1 N NaHSO4, filtered, washed with water, and dried in vacuo to provide the title compound as a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (ddd, J=15.28, 11.80, 7.14 Hz, 1 H), 1.67 (s, 3 H), 1.79-1.89 (m, 2 H), 1.90-2.00 (m, 1 H), 3.26-3.31 (m, 2 H), 3.33-3.40 (m, 1 H), 3.56 (ddd, J=13.91, 5.95, 4.30 Hz, 1 H), 3.64-3.71 (m, 1 H), 3.76-3.84 (m, 1 H), 3.96-4.04 (m, 1 H), 4.15 (s, 2 H), 4.27 (t, J=6.77 Hz, 2 H), 7.11-7.17 (m, 2 H), 7.38-7.44 (m, 2 H), 8.03 (t, J=5.85 Hz, 1 H), 8.19 (d, J=1.46 Hz, 1 H), 8.56 (d, J=1.46 Hz, 1 H), 10.42 (t, J=5.58 Hz, 1 H); ES+ MS: 483 (M+H+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe resulting residue was treated with 1 N NaHSO4
  3. filtrationfiltered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3c596454a84e482bae1f55801ff53e9d
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…