Dichloromethane → HCID 66739331, compound

HRID 1402760Notes

Reaction equation

HRID 1402760 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([CH:14]3[CH2:17][N:16]([C:18]([C:20]4[NH:24][C:23]5[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=5[N:21]=4)=[O:19])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH3:31]OS(OC)(=O)=O.C(Cl)Cl>C1COCC1.CO>[NH3:5].[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([CH:14]3[CH2:15][N:16]([C:18]([C:20]4[N:21]([CH3:31])[C:22]5[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=5[N:24]=4)=[O:19])[CH2:17]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 46852135HCID 46852135, compound

Product 2

HCID 222AmmoniaHCID 66739331HCID 66739331, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-({3-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-1-yl}carbonyl)-1H-benzimidazole (170 mg, 0.45 mmol) in THF (10 ml) was added NaOH (1.12 ml of a 2.5 M aqueous solution, 2.8 mmol). After 5 minutes, dimethylsulfate (0.2 ml, 2.1 mmol) was added and the reaction was stirred at room temperature for 16 hours. The reaction was then concentrated at reduced pressure and purified directly via FCC (using a gradient of eluents; 98:2 to 95:5 DCM:2M NH3 in MeOH) to give the title compound (45 mg, 25% yield) as yellow oil.

Workup

  1. concentrationThe reaction was then concentrated at reduced pressure
  2. custompurified directly via FCC (

Sources & evidence

ORD record
ord-4d9afbb74bf64c7d8a62442ac7efea7d
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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