Potassium Carbonate → HCID 10278765, compound

HRID 970891Notes

Reaction equation

HRID 970891 reaction equation
C([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17]Cl)(OC(C)(C)C)=O.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][NH:26][C:27](=[O:46])[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH:35][CH:36]2[C:45]3[N:44]=[CH:43][CH:42]=[CH:41][C:40]=3[CH2:39][CH2:38][CH2:37]2)=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.C(OCC)(=O)C>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[CH2:17][N:35]([CH2:34][C:31]1[CH:32]=[CH:33][C:28]([C:27]([NH:26][CH2:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)=[O:46])=[CH:29][CH:30]=1)[CH:36]1[C:45]2[N:44]=[CH:43][CH:42]=[CH:41][C:40]=2[CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10133884HCID 10133884, compoundHCID 15829159tert-Butyl 2-(chloromethyl)-1H-benzimidazole-1-carboxylate

Product 1

HCID 10278765HCID 10278765, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-BOC-chloromethyl benzimidazole (215 mg, 0.84 mmol), N-Pyridin-2-ylmethyl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzamide (AMD9363) (300 mg, 0.84 mmol), and K2CO3 (346 mg, 2.50 mmol) were heated to reflux in CH3CN (4 mL) for 24 hours under N2. The reaction mixture was diluted with 200 mL ethyl acetate, and washed with sat. NaHCO3, then brine, and dried over Na2SO4. Evaporation of the solvent and purification of the residue by flash chromatography on silica gel, followed by radial chromatography on silica gel (1 mm plate, 3:3:94 CH3OH—NH3 H2O—CH2Cl2,), afforded the free base of the title compound (120 mg, 28%) as pale yellow oil.

Workup

  1. washwashed with sat. NaHCO3
  2. dry with materialbrine, and dried over Na2SO4
  3. customEvaporation of the solvent and purification of the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-7f191e783b904961903786b96edffd07
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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