Triethylamine → HCID 20773307, compound

HRID 1814798Notes

Reaction equation

HRID 1814798 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[CH3:10][C@H:11]1[CH2:16][NH:15][C@H:14]([CH3:17])[CH2:13][N:12]1[C:18](=[O:26])[C@:19]([OH:25])([CH3:24])[C:20]([F:23])([F:22])[F:21].C(N(CC)CC)C>CCOC(C)=O>[CH3:10][C@H:11]1[CH2:16][N:15]([S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:8])=[O:7])[C@H:14]([CH3:17])[CH2:13][N:12]1[C:18](=[O:26])[C@:19]([OH:25])([CH3:24])[C:20]([F:23])([F:21])[F:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 10587022HCID 10587022, compound

Product 1

HCID 20773307HCID 20773307, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-thiophene sulphonyl chloride (129 mg, 0.707 mmol) in EtOAc (10 ml) was added to a stirred mixture 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) (150 mg, 0.59 mmol) and triethylamine (0.125 ml, 0.886 mmol) in EtOAc (15 ml). The resultant mixture was stirred at ambient temperature for 4 hours, washed with 1 M hydrochloric acid, saturated sodium hydrogen carbon solution and brine, dried and evaporated. The residue was recrystallized from EtOAc/hexane to give the title compound as a solid (71 mg, 0.18 mmol). Mp: 116-117° C.; NMR: 0.95 (d, 3H), 1.25 (dd, 3H), 1.65 (s, 3H), 3.2 (s, 3H), 3.3 (s, 1H), 3.5 (dd, 1H), 4.05 (s, 1H), 4.15 (s, 1H), 4.3 (s, 1H), 4.75 (s, 1H), 7.0 (dd, 1H), 7.5 (dd, 2H); m/z 399.

Workup

  1. washwashed with 1 M hydrochloric acid, saturated sodium hydrogen carbon solution and brine
  2. customdried
  3. customevaporated
  4. customThe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-cbde64d22b3d45f3ada0b327636ae631
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

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