Potassium Carbonate → HCID 67923019, compound

HRID 2082439Notes

Reaction equation

HRID 2082439 reaction equation
[CH2:1]1[C:6]2[C:7]3[N:8]([CH:19]=[N:20][N:21]=3)[C:9]3[CH:17]=[CH:16][C:15](=[O:18])[CH2:14][C:10]=3[N:11]3[CH:12]=[CH:13][C:4]([C:5]=23)=[CH:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][CH:30]1[CH2:32][CH2:31]1>CN(C)C=O>[CH:30]1([CH2:29][CH:14]2[C:10]3[N:11]4[CH:12]=[CH:13][C:4]5[C:5]4=[C:6]([CH2:1][CH2:2][CH:3]=5)[C:7]4[N:8]([CH:19]=[N:20][N:21]=4)[C:9]=3[CH:17]=[CH:16][C:15]2=[O:18])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 67858201HCID 67858201, compound

Product 1

HCID 67923019HCID 67923019, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

1,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,2,4]triazolo[4,3-d][1,4]benzodiazepin-8(7H)-one (5.2 g) was dissolved in dimethylformamide (150 ml). Potassium carbonate (0.5 g) was added, followed by (chloromethyl)cyclopropane (2.1 ml). The mixture was stirred at 95° C. overnight, filtered, and evaporated under reduced pressure. The residue was purified by high performance liquid chromatography (1% methanol/dichloromethane) to yield 3.4 g (54.8%) of product. Recrystallization from pentane/ether gave the analytical sample, mp 99° C.

Workup

  1. filtrationfiltered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by high performance liquid chromatography (1% methanol/dichloromethane)

Sources & evidence

ORD record
ord-e17bca502cb5477aad2deb27ca34cb6e
Source dataset
uspto-grants-1993_02
Patent number
US05189161

Reaction notes

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