2-Amino-2-thioxoethyl 2,2-dimethylpropanoate → 8-Chloro-7-dimethylamino-4-[3-(2-hydroxymethyl-thiazol-4-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265923Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH2:17][C:16](=[O:18])[NH:15][C:14]3[CH:19]=[C:20]([Cl:26])[C:21]([N:23]([CH3:25])[CH3:24])=[CH:22][C:13]=3[N:12]=2)[CH:8]=[CH:9][CH:10]=1)=O.C(C([O:33][CH2:34][C:35]([NH2:37])=[S:36])=O)(C)(C)C>CCO.CCOC(C)=O>[Cl:26][C:20]1[C:21]([N:23]([CH3:24])[CH3:25])=[CH:22][C:13]2[N:12]=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([C:3]4[N:37]=[C:35]([CH2:34][OH:33])[S:36][CH:2]=4)[CH:6]=3)[CH2:17][C:16](=[O:18])[NH:15][C:14]=2[CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(3-bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one (0.22 g) and 2-(tert.-butylcarbonyl-oxy)thioacetamide (0.11 g) in EtOH (3 mL) was heated at 80° C. for 0.5 h. The solution was diluted with AcOEt, washed with sat. NaHCO3 solution and with brine, dried and evaporated. The residue was stirred in a mixture of MeOH (8 mL) and 1.5N KOH (8 mL) at 20° C. for 20 min. H2O (30 ml) was added and the precipitated product collected by filtration to give the title compound (0.9 g) as yellow powder.

Workup

washwashed with sat. NaHCO3 solution and with brine
customdried
customevaporated
additionH2O (30 ml) was added
filtrationthe precipitated product collected by filtration

Sources & evidence

ORD record: ord-5c67aa87c0604b1690508b06bfb7705d
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544985B2

Reaction notes

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