Diisopropylcarbodiimide → N-{4-Chloro-3-[3-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-2,2-dimethyl-propionamide

HRID 1258677Notes

Reaction equation

HRID 1258677 reaction equation
CC(C)N=C=NC(C)C.[Cl:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][C:12]=1[NH:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([N:35]2[CH2:40][CH2:39][CH:38]([C:41]([F:44])([F:43])[F:42])[CH2:37][CH2:36]2)[CH:32]=[CH:31][C:30]=1[NH:45][CH3:46])=S>CC#N>[Cl:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][C:12]=1[NH:25][CH:26]1[NH:28][C:29]2[CH:34]=[C:33]([N:35]3[CH2:40][CH2:39][CH:38]([C:41]([F:44])([F:43])[F:42])[CH2:37][CH2:36]3)[CH:32]=[CH:31][C:30]=2[N:45]1[CH3:46]

Participants

4

Reactant 2

HCID 12734Diisopropylcarbodiimide2×HCID 86674333HCID 86674333, compound

Product 1

HCID 71074099N-{4-Chloro-3-[3-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

DIC (130 μL, 0.8 mmol) was added to N-(4-chloro-3-{3-[2-methylamino-5-(4-trifluoromethyl-piperidin-1-yl)-phenyl]-thioureido}-benzyl)-2,2-dimethyl-propionamide (180 mg, 0.3 mmol) in MeCN. The reaction mixture was heated at 60° C.-80° C. for one week (additional DIC (2.5 ml) was added). The mixture was cooled to rt and concentrated. The residue was treated with MeCN, filtered and washed. The filtercake was diluted with dioxane and HCOOH and lyophilized to give the title compound.

Workup

  1. temperatureThe reaction mixture was heated at 60° C.-80° C. for one week
  2. concentrationconcentrated
  3. additionThe residue was treated with MeCN
  4. filtrationfiltered
  5. washwashed
  6. additionThe filtercake was diluted with dioxane and HCOOH

Sources & evidence

ORD record
ord-b636b1e90650475a9ea9a44ac5840d7b
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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