Water → HCID 22645708, compound

HRID 2414355Notes

Reaction equation

[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[C:24]([F:25])=[C:23]([CH2:26][O:27][C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29])[C:22]([F:34])=[C:21]([NH:35][C:36](=[O:39])[CH2:37]Cl)[C:17]=3[C:18](=[O:20])[CH:19]=2)=[CH:10][C:9]=1[F:40])=[O:6])[CH:2]=[CH2:3].Cl.[CH3:42][NH:43][CH3:44].C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[C:24]([F:25])=[C:23]([CH2:26][O:27][C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29])[C:22]([F:34])=[C:21]([NH:35][C:36](=[O:39])[CH2:37][N:43]([CH3:44])[CH3:42])[C:17]=3[C:18](=[O:20])[CH:19]=2)=[CH:10][C:9]=1[F:40])=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-[4-(allyloxycarbonyl)amino-3-fluorophenyl]-7-[(allyloxycarbonyl)oxy]methyl-5-(chloroacetamido)-6,8-difluoro-4H-1-benzopyran-4-one (2.12 g, 3.65 mmol) in dimethylformamide (40 mL) were added dimethylamine hydrochloride (1.49 g, 18.3 mmol) and diisopropylethylamine (3.2 mL, 18 mmol), and the mixture was stirred at 50° C. for 2 hours. Water was added thereto, and the mixture was extracted with ethyl acetate to afford 2-[4-(allyloxycarbonyl)amino-3-fluorophenyl]-7-[(allyloxycarbonyl)oxy]methyl-5-(dimethylamino)acetamido-6,8-difluoro-4H-1-benzopyran-4-one (2.12 g, 99%)

Workup

extractionthe mixture was extracted with ethyl acetate

Sources & evidence

ORD record: ord-7f488e2d63524264a2aed6502df5a579
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812246B2

Reaction notes

Loading…