Ethanol → HCID 178501188, compound

HRID 518600Notes

Reaction equation

HRID 518600 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH2:22]1.CCO.[N:34]#[C:35]Br>C(Cl)Cl>[NH2:34][C:35]1[N:20]([C@@H:21]2[CH2:22][CH2:23][C@H:24]([C:27]([O:29][CH3:30])=[O:28])[CH2:25][CH2:26]2)[C:3]2[CH:4]=[C:5]([CH2:8][O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:11]([CH3:12])[CH3:13])[CH:14]([CH3:16])[CH3:15])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10476Cyanogen BromideHCID 178501198HCID 178501198, compound

Product 1

HCID 178501188HCID 178501188, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask under nitrogen atmosphere was charged with cis-methyl 4-(2-amino-5-((triisopropylsilyloxy)methyl)phenylamino)cyclohexanecarboxylate (2.5 g, 5.75 mmol) and EtOH (23.96 mL) To this was added cyanogen bromide (0.914 g, 8.63 mmol), and the reaction mixture was stirred overnight at RT. The reaction mixture was diluted with DCM (80 mL) and washed with 1N aqueous NaOH (50 mL). The organic layer was collected, dried over sodium sulfate, and concentrated to dryness to afford cis-methyl 4-(2-amino-6-((triisopropylsilyloxy)methyl)-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate as a brown solid (2.64 g, 100% yield). MS m/z=460.2 [M+H]. Calc'd for C25H41N3O3Si: 459.3.

Workup

  1. washwashed with 1N aqueous NaOH (50 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9557fbbb554542808379066f7b017408
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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