Dimethylacetamide → HCID 9803868, compound

HRID 1635632Notes

Reaction equation

HRID 1635632 reaction equation
CC(N(C)C)=O.[CH3:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH3:14])[N:9]1[CH2:15][CH2:16][NH:17][C:18]([C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]1)=[O:19].Cl[C:27]1[N:31](C(OC(C)(C)C)=O)[C:30]2[CH:39]=[CH:40][C:41]([C:43]([F:46])([F:45])[F:44])=[CH:42][C:29]=2[N:28]=1>C1(C)C(C)=CC=CC=1>[CH2:8]([NH:9][CH2:10][CH3:11])[CH3:7].[CH3:14][C@H:10]1[CH2:11][CH2:12][CH2:13][C@@H:8]([CH3:7])[N:9]1[CH2:15][CH2:16][NH:17][C:18]([C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]1[C:27]1[NH:28][C:29]2[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[CH:39][C:30]=2[N:31]=1)=[O:19]

Participants

6

Reactant 3

HCID 31374DimethylacetamideHCID 12096144HCID 12096144, compoundHCID 12096145HCID 12096145, compound

Product 2

HCID 8021DiethylamineHCID 9803868HCID 9803868, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
80 °C

Procedure

Dimethylacetamide (0.5 ml) was added to a mixture of (2S)-N2-2-[(cis)-2,6-dimethyl-1-piperidinyl]ethyl-2-piperidinecarboxamide (134 mg) [see Preparation 15] and tert-butyl chloro-5-(trifluoromethyl)-1H-1,3-benzimidazole-1-carboxylate (463 mg) [see Preparation 16]. The reaction mixture was heated to 80° C. for 12 hours, after which time the mixture was reduced to low volume, xylene (50 ml) was added, and all solvent was removed under reduced pressure. The residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate, the organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0, changing to 98:2, by volume, ethyl acetate:diethylamine, in 0.5% increments, to afford (2S)-N2-2-[(cis)-2,6-dimethyl-1-piperidinyl]ethyl-1-[6-(trifluoromethyl)-1H-1,3-benzimidazol-2-yl]-2piperidinecarboxamide (55 mg) as a white solid.

Workup

  1. additionwas added
  2. customall solvent was removed under reduced pressure
  3. customThe residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  4. customthe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0

Sources & evidence

ORD record
ord-22da5c3bba3848c2b92afafe28ea0d4f
Source dataset
uspto-grants-2003_01
Patent number
US06509464B1

Reaction notes

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