Triethylamine → HCID 69119459, compound

HRID 1814802Notes

Reaction equation

HRID 1814802 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:13])[F:12].C(N(CC)CC)C.[CH3:25][N:26]([CH3:38])[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)=[O:28]>CCOC(C)=O>[CH3:1][C@H:2]1[CH2:7][N:6]([C:33](=[O:34])[C:32]2[CH:31]=[CH:30][C:29]([C:27](=[O:28])[N:26]([CH3:38])[CH3:25])=[CH:37][CH:36]=2)[C@H:5]([CH3:8])[CH2:4][N:3]1[C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:12])[F:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10587022HCID 10587022, compoundHCID 224988444-(Dimethylcarbamoyl)benzoyl chloride

Product 1

HCID 69119459HCID 69119459, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of (R)-[(2S,5R)-2-methyl-5-methyl-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (J. Med. Chem., 1999, 42, 2741-2746) (400 mg, 1.57 mmol) and triethylamine (0.4 ml, 2.84 mmol) in EtOAc (25 ml) was added a solution of 4-dimethylcarbamoylbenzoyl chloride (350 mg, 1.66 mmol) in EtOAc (25 ml). The resultant mixture was stirred at ambient temperature for 24 hours, washed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was chromatographed on silica with EtOAc as eluent to give the title compound as a solid (120 mg, 0.28 mmol). NMR: 1.1-1.13 (m, 6H), 1.6 (s, 3H), 2.9 (s, 3H), 3.1 (s, 3H), 3.25 (m, 1H), 3.4 (m, 1H), 4.25 (s, 2H), 4.65 (s, 1H), 4.9 (s, 1H), 5.2 (s, 1H), 7.3-7.4 (dd, 4H); m/z 428.

Workup

  1. washwashed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on silica with EtOAc as eluent

Sources & evidence

ORD record
ord-6de9a55db8844c7b8e7679d6f1658edc
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

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