Diisopropylethylamine → HCID 69480330, compound

HRID 2364419Notes

Reaction equation

HRID 2364419 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.[N:44]1([C:50](Cl)=[O:51])[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>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:50]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[O:51])=[N:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 69482180HCID 69482180, compound

Product 1

HCID 69480330HCID 69480330, 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 4-morpholinecarbonyl chloride (0.008 mL, 0.068 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 an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.3 (s, 1 H), 3.10 (s, 2 H), 3.13-3.22 (m, 8 H), 3.27-3.33 (m, 1 H), 3.42-3.50 (m, 4 H), 3.55 (d, J=10.67 Hz, 2 H), 3.63-3.73 (m, 2 H), 3.78 (d, J=4.49 Hz, 1 H), 3.93-4.05 (m, 2 H), 4.14 (s, 2 H), 4.30 (t, J=6.67 Hz, 2 H), 7.11-7.19 (m, 2 H), 7.39-7.47 (m, 2 H), 8.34 (s, 1 H), 8.57 (d, J=1.12 Hz, 1 H), 9.88 (br. s., 1 H), 10.38-10.48 (m, 1 H); ES+ MS: 583 (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-aacca684b7ba4d30a68ba71910e724c6
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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