Triethylamine → HCID 25105790, compound

HRID 1675349Notes

Reaction equation

HRID 1675349 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[S:12][C:11]([N:13]2[CH2:20][C:19]3[CH2:18][NH:17][CH2:16][C:15]=3[CH2:14]2)=[N:10][CH:9]=1)=[O:7].FC(F)(F)C([O-])=O.C(N(CC)CC)C.[F:36][C:37]([F:48])([F:47])[C:38]1[CH:46]=[CH:45][CH:44]=[CH:43][C:39]=1[C:40](Cl)=[O:41]>CN(C=O)C>[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[S:12][C:11]([N:13]2[CH2:14][C:15]3[CH2:16][N:17]([C:40](=[O:41])[C:39]4[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=4[C:37]([F:36])([F:47])[F:48])[CH2:18][C:19]=3[CH2:20]2)=[N:10][CH:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 84468TrifluoroacetateHCID 58459774HCID 58459774, compound

Product 1

HCID 25105790HCID 25105790, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-Methylbutyl)-2-(3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl)thiazole-5-carboxamide, trifluoroacetate (220 mg, 0.52 mmol) and triethylamine (0.22 ml, 1.57 mmol) were dissolved in 10 ml of DMF and admixed in an ice bath with 2-trifluoromethylbenzoyl chloride (218 mg, 1.04 mmol). The mixture was stirred further for 1 h and allowed to warm to room temperature, and concentrated, water and ethyl acetate were added and the organic phase was removed, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 25 mg (10%), M+H+: 479.06.

Workup

  1. concentrationconcentrated
  2. additionwater and ethyl acetate were added
  3. customthe organic phase was removed
  4. concentrationconcentrated
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-8c2d3f58ac7d42dfa9ed3f1135866cfe
Source dataset
uspto-grants-2011_08
Patent number
US08003677B2

Reaction notes

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