Ethylthiourea → 8-Chloro-7-dimethylamino-4-[3-(2-ethylamino-thiazol-4-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265925Notes

Reaction equation

HRID 1265925 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.[CH2:27]([NH:29][C:30]([NH2:32])=[S:31])[CH3:28]>C1COCC1.CCOC(C)=O>[Cl:26][C:20]1[C:21]([N:23]([CH3:25])[CH3:24])=[CH:22][C:13]2[N:12]=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([C:3]4[N:32]=[C:30]([NH:29][CH2:27][CH3:28])[S:31][CH:2]=4)[CH:6]=3)[CH2:17][C:16](=[O:18])[NH:15][C:14]=2[CH:19]=1

Participants

5

Reactant 2

HCID 3032338EthylthioureaHCID 186132344-(3-Bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 186132668-Chloro-7-dimethylamino-4-[3-(2-ethylamino-thiazol-4-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-oneYield 18.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(3-bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one (130 mg) (Example 193a) and N-ethyl-thiourea (31 mg) in THF (3 mL) was heated at 60° C. for 15 min. The mixture was diluted with AcOEt and washed with sat. NaHCO3 solution and with brine. The organic layer was dried and evaporated and the residue was purified by chromatography on silica gel using AcOEt/hexane (1:1) as eluent. The purified product was triturated with Et2O to give the title compound (24 mg) as yellow solid.

Workup

  1. washwashed with sat. NaHCO3 solution and with brine
  2. customThe organic layer was dried
  3. customevaporated
  4. customthe residue was purified by chromatography on silica gel
  5. customThe purified product was triturated with Et2O

Sources & evidence

ORD record
ord-89dc9320dc1e44cf92bb308e978ae586
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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