Reaction #83510

Reaction equation

α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

2-dimethylaminoethanethiol hydrochloride

triethylamine

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

→

beige solid

Yield 93.1%

α-[[2-(Dimethylamino)ethyl]thio]-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

Yield 93.1%

Solvents

methyl alcohol

Conditions

Workup

1. 1
   OtherThe methyl alcohol is evaporated
2. 2
   workup.ADDITIONthe residue diluted with water
3. 3
   FiltrationThe resulting suspension is filtered
4. 4
   Washthe precipitate washed with water
5. 5
   workup.DISSOLUTIONThe solid is dissolved in ethyl acetate
6. 6
   Washwashed with saturated NaHCO3, brine
7. 7
   Dryingdried with Na2SO4
8. 8
   FiltrationThe mixture is filtered
9. 9
   Otherthe filtrate evaporated in vacuo to a residue which

Procedure

A mixture of 0.14 g of α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide, 0.47 g of 2-dimethylaminoethanethiol hydrochloride in 2 ml of methyl alcohol, 0.30 g of triethylamine and 3 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is heated at 60° C. for 48 hours. The methyl alcohol is evaporated and the residue diluted with water. The resulting suspension is filtered and the precipitate washed with water. The solid is dissolved in ethyl acetate and washed with saturated NaHCO3, brine and dried with Na2SO4. The mixture is filtered and the filtrate evaporated in vacuo to a residue which is stirred with ether-hexane to give 0.15 g of beige solid. MS(CI): 525(M+H).

Source