Methyl chloroformate → HCID 86612784, compound

HRID 2364417Notes

Reaction equation

HRID 2364417 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.Cl[C:45]([O:47][CH3:48])=[O:46]>CN(C=O)C>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:11]2[CH:12]=[C:13]3[C:8]([C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][N:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)=[O:24])[C:5](=[O:34])[N:4]3[CH2:3][CH2:2][NH:1][C:45](=[O:46])[O:47][CH3:48])=[N:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 69482180HCID 69482180, compound

Product 1

HCID 86612784HCID 86612784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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, 0.052 mmol) and diisopropyl ethylamine (0.05 mL, 0.29 mmol) in DMF (5 mL) under nitrogen was treated with methyl chloroformate (0.0087 mL, 0.11 mmol) at 40° C. for 1 h then 3½ h at ambient temperature. The reaction was concentrated in vacuo and the resulting residue was triturated with Et2O:MeOH, filtered, washed with 2:1 Et2O:MeOH, and dried in vacuo to provide the title compound as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.23 (s, 1 H), 3.06-3.20 (m, 2 H), 3.25-3.32 (m, 2 H), 3.36-3.43 (m, 2 H), 3.45 (s, 3 H), 3.55 (d, J=10.95 Hz, 2 H), 3.69 (t, J=12.2 Hz, 2 H), 3.78 (d, J=6.74 Hz, 2 H), 4.00 (d, J=12.35 Hz, 2 H), 4.15 (s, 2 H), 4.31 (t, J=5.76 Hz, 2 H), 7.12-7.19 (m, 2 H), 7.38-7.45 (m, 2 H), 8.16 (s, 1 H), 8.55 (s, 1 H), 9.91 (br. s., 1 H), 10.39 (t, J=6.60 Hz, 1 H); ES+ MS: 528 (M+H+).

Workup

  1. custom3½ h
  2. customat ambient temperature
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe resulting residue was triturated with Et2O
  5. filtrationMeOH, filtered
  6. washwashed with 2:1 Et2O
  7. dry with materialMeOH, and dried in vacuo

Sources & evidence

ORD record
ord-8908c85b1b104436b34d22e2d146a531
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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