4-Pyridylthiourea → 8-Chloro-7-dimethylamino-4-{3-[2-(pyridin-4-ylamino)-thiazol-4-yl]-phenyl}-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265927Notes

Reaction equation

HRID 1265927 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.[N:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH2:36])=[S:35])=[CH:29][CH:28]=1>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:36]=[C:34]([NH:33][C:30]5[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=5)[S:35][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 27372494-PyridylthioureaHCID 186132344-(3-Bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 186135028-Chloro-7-dimethylamino-4-{3-[2-(pyridin-4-ylamino)-thiazol-4-yl]-phenyl}-1,3-dihydro-benzo[b][1,4]diazepin-2-oneYield 37.6%

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 1-(4-pyridyl)-2-thiourea (46 mg) in THF (3 mL) was heated at 60° C. for 45 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 triturated with Et2O to give the title compound (55 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 triturated with Et2O

Sources & evidence

ORD record
ord-38e8eed7f22c4f33860e1d31f22fa009
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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