Sodium Methoxide → HCID 22636109, compound

HRID 2415719Notes

Reaction equation

C[O-].[Na+].C([O:7][C:8]1[CH:9]=[C:10]([CH:37]=[CH:38][CH:39]=1)[C:11]([NH:13][C:14]1[CH:15]=[C:16]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:17]([NH:19][C:20]1[CH:25]=[C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:23]=[C:22]([F:32])[CH:21]=1)=[O:18])=[O:12])(=O)C>CO>[Cl:36][C:35]1[CH:34]=[CH:33][C:16]([C:17]([NH:19][C:20]2[CH:25]=[C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:23]=[C:22]([F:32])[CH:21]=2)=[O:18])=[CH:15][C:14]=1[NH:13][C:11](=[O:12])[C:10]1[CH:37]=[CH:38][CH:39]=[C:8]([OH:7])[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium methoxide (95%, 0.26 g) was added to a stirred solution of 3-(3-acetoxybenzamido)-4-chloro-N-(3-fluoro-5-morpholinophenyl)benzamide (1.23 g) in methanol (75 ml) which had been cooled to 0° C. The resultant solution was stirred at ambient temperature for three hours. The mixture was concentrated by evaporation to a volume of about 15 ml and water (20 ml) was added. The solution was acidified to pH3 by the addition of 1N aqueous hydrochloric acid solution. The precipitate so formed was isolated and dried under vacuum. There was thus obtained the title compound (0.86 g); NMR Spectrum: (DMSOd6) 2.47 (s, 3H), 3.08 (t, 4H), 3.7 (t, 4H), 6.53 (d, 1H), 6.98 (m, 1H), 7.14 (s, 1H), 7.19 (d, 1H), 7.33 (m, 1H), 7.42 (d, 1H), 7.70 (d, 1H), 7.84 (m, 1H), 8.15 (d, 1H), 9.75 (s, 1H), 10.08 (s, 1H), 10.29 (s, 1H); Mass Spectrum: M+H+ 470.

Workup

concentrationThe mixture was concentrated by evaporation to a volume of about 15 ml and water (20 ml)
additionwas added
additionThe solution was acidified to pH3 by the addition of 1N aqueous hydrochloric acid solution
customThe precipitate so formed
customwas isolated
customdried under vacuum

Sources & evidence

ORD record: ord-e06d9e669da5498ba7beaa1351dd5a97
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821965B1

Reaction notes

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