HCID 11373168, compound → HCID 22562198, compound

HRID 982629Notes

Reaction equation

HRID 982629 reaction equation
Cl[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:9][CH2:8]2)[C:5]2[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=2[N:3]=1.[C:30]([O:34][C:35]([N:37]1[CH:42]2[CH2:43][CH2:44][CH:38]1[CH2:39][NH:40][CH2:41]2)=[O:36])([CH3:33])([CH3:32])[CH3:31]>CO>[C:20]1([C:13]2([N:10]3[CH2:11][CH2:12][CH:7]([N:6]4[C:5]5[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=5[N:3]=[C:2]4[N:40]4[CH2:41][CH:42]5[N:37]([C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:36])[CH:38]([CH2:44][CH2:43]5)[CH2:39]4)[CH2:8][CH2:9]3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 11373168HCID 11373168, compoundHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Product 1

HCID 22562198HCID 22562198, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-1-[1-(1-phenylcycloheptyl)-4-piperidinyl]-1H-benzimidazole (0.12 g, 0.294 mmol), 8-t-butoxycarbonyl-3,8-diazabicyclo[3.2.1]octane (0.12 g, 0.565 mmol,: D.Barlocco et al, J. Med. Chem. 1998, 41, 674), and methanol (1.5 ml) was stirred in a sealed tube at 120° C. for 4 days. After cooling down to room temperature, the reaction mixture was concentrated and purified by preparative TLC (1 mm plate×2, developed by CH2Cl2/MeOH: 10/1) to give 0.1269 g (74%) of an oil.

Workup

  1. temperatureAfter cooling down to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. custompurified by preparative TLC (1 mm plate×2, developed by CH2Cl2/MeOH: 10/1)

Sources & evidence

ORD record
ord-275df5aeef994a3cb4e223f5b29581e8
Source dataset
uspto-grants-2005_03
Patent number
US06861425B2

Reaction notes

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