Dimethylamine → HCID 20773300, compound

HRID 1814799Notes

Reaction equation

HRID 1814799 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C@H:8]1[CH2:13][N:12]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C@H:11]([CH3:26])[CH2:10][N:9]1[C:27](=[O:35])[C@:28]([OH:34])([CH3:33])[C:29]([F:32])([F:31])[F:30].[CH3:36][NH:37][CH3:38].CCOC(C)=O>C(Cl)Cl>[CH3:7][C@H:8]1[CH2:13][N:12]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23](=[O:24])[N:37]([CH3:38])[CH3:36])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[C@H:11]([CH3:26])[CH2:10][N:9]1[C:27](=[O:35])[C@:28]([OH:34])([CH3:33])[C:29]([F:30])([F:31])[F:32]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 9932837HCID 9932837, compound

Product 1

HCID 20773300HCID 20773300, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.08 ml, 0.88 mmol) was added to a solution of (R)-[(2S,5R)-2-methyl-5-methyl-4-(4-carboxyphenylsulphonyl)-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (320 mg, 0.73 mmol) (Example 4) in DCM (25 ml). The resultant mixture was stirred at ambient temperature for 4 hours, evaporated to dryness, the residue treated with 40% aqueous dimethylamine (0.82 ml, 7.3 mmol) and the resultant mixture was stirred at ambient temperature overnight. The mixture was treated with EtOAc (25 ml), washed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was chromatographed on silica with 50% EtOAc in DCM as eluent to give a solid which was recrystallized from EtOAc/hexane to give the title compound as a solid (26 mg, 0.056 mmol). Mp: 86-87° C.; NMR: 0.95 (d, 3H), 1.25 (dd, 3H), 1.65 (s, 3H), 2.95 (s, 3H), 3.1 (s, 3H), 3.25 (dd, 1H), 3.5 (dd, 1H), 4.2 (m, 2H), 4.5 (s, 1H), 4.8 (s, 1H), 7.5 (d, 2H), 7.85 (d, 2H); m/z: 464.

Workup

  1. customevaporated to dryness
  2. washwashed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on silica with 50% EtOAc in DCM as eluent
  6. customto give a solid which
  7. customwas recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-307868e6269c4bcea946d339a2227ca2
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

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