Dichloromethane → HCID 21915274, compound

HRID 2117954Notes

Reaction equation

HRID 2117954 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:27][C:28](=[O:30])[CH3:29])[S:14][C:15]=2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[N:31]#[C:32]Br.[OH-].[Na+].C(Cl)Cl>CO.CCOCC>[NH2:31][C:32]1[NH:1][C:2]2[CH:3]=[C:4]([CH2:9][CH2:10][C:11]3[N:12]=[C:13]([NH:27][C:28](=[O:30])[CH3:29])[S:14][C:15]=3[CH2:16][C:17]3[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=3)[CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 21914779HCID 21914779, compound

Product 1

HCID 21915274HCID 21915274, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of N-{4-[2-(3,4-diaminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (70.8 mg) in MeOH (0.7 ml) was added cyanogen bromide (25.3 mg), then the mixture was stirred for 14 h at 20° C. To the reaction mixture was added 1N—NaOH (0.239 ml) and the mixture was concentrated in vacuo. To the residue was added CHCl3:MeOH=10:1 (10 ml), and an insoluble material was removed by filtration. The filtrate was purified by flash column chromatography over NH silica gel with CHCl3/MeOH (100:1→10:1) as an eluent to give colorless oil. The oil was solidified with CH2Cl2: Et2O=2:1 to give N-{4-[2-(2-amino-1H-benzimidazol-6-yl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionTo the residue was added CHCl3
  3. customMeOH=10:1 (10 ml), and an insoluble material was removed by filtration
  4. customThe filtrate was purified by flash column chromatography over NH silica gel with CHCl3/MeOH (100:1→10:1) as an eluent
  5. customto give colorless oil

Sources & evidence

ORD record
ord-5faf11b2dfe24513bdeee3afa8acc4d2
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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