Hydrochloric Acid → HCID 69320417, compound

HRID 1767496Notes

Reaction equation

[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[H][H].[CH2:16]([N:23]1[C:28]2[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=2[C:26](=O)[O:25]C1=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CC(N(C)C)=O>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[N:23]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:28]2[C:27]([C:26]=1[OH:25])=[CH:32][C:31]([F:33])=[CH:30][CH:29]=2)=[O:4])[CH3:7]

Participants

Conditions

Temperature: 90 °C

Procedure

Neat diethyl malonate (0.89 mL, 5.8 mmol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 256 mg, 6.41 mmol) in dimethylacetamide under N2 atmosphere. The mixture was stirred at room temperature until the evolution of hydrogen gas ceased, then the mixture was heated to 90° C. for 30 min and cooled to room temperature. A solution of Compound 36 (1.74 g, 6.41 mmol) in dimethylacetamide was added slowly to the mixture, which was heated overnight at 110° C. The mixture was cooled to room temperature, poured into ice water, and acidified by cold 10% HCl. The solids formed were filtered, washed several times by water, and dried at room temperature under vacuum to yield 1.4 g (64%) of white solids. M.P. 129° C. 1H NMR (DMSO-d6): δ 1.30 (t, J=6.9 Hz, 3H), 4.34 (q, J=6.9 Hz, 2H), 5.46 (s, 2H), 7.17–7.24 (m, 5H), 7.38 (dd, J=4.6, 9.6 Hz, 1H), 7.50 (td, J=2.9, 8.3 Hz, 1H), 7.80 (dd, J=3.1, 9.4 Hz, 1H). EIMS m/z 342 (M+1), 364 (M+23). Anal. (C19H16FNO4) C, H, N.

Workup

temperaturecooled to room temperature
temperaturewas heated overnight at 110° C
temperatureThe mixture was cooled to room temperature
customThe solids formed
filtrationwere filtered
washwashed several times by water
customdried at room temperature under vacuum

Sources & evidence

ORD record: ord-db7b9ace85f84fe9afcecb64e4987abc
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235546B2

Reaction notes

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