Trifluoroacetic acid → HCID 25175938, compound

HRID 2190346Notes

Reaction equation

HRID 2190346 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([NH:21][C:22](=[O:47])[N:23]([CH2:32][CH2:33][CH:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[S:18][C:19]=2[Cl:20])=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:20][C:19]1[S:18][C:17]([NH:21][C:22](=[O:47])[N:23]([CH2:32][CH2:33][CH:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[N:16][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57586388HCID 57586388, compound

Product 1

HCID 25175938HCID 25175938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-4-(5-chloro-2-(((3,3-diphenylpropyl)(2-(2-pyridinyl)ethyl)carbamoyl)amino)-1,3-thiazol-4-yl)benzenesulfonamide 84 (0.187 g, 0.272 mmol) in DCM (1 mL) was added anisol (0.20 mL) and TFA (2 mL). The reaction mixture was stirred at room temperature for 1 d and concentrated. The concentrate was diluted with EtOAc and the organic phase was washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by crystallization from a mixture of DCM and hexanes gave 4-(5-chloro-2-(((3,3-diphenylpropyl)(2-(2-pyridinyl)ethyl)carbamoyl)amino)-1,3-thiazol-4-yl)benzenesulfonamide 85. Mass spectrum, calculated for C32H30ClN5O3S2 631.2; found 632.1 (M++1).

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with EtOAc
  3. washthe organic phase was washed with saturated NaHCO3 (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. customby crystallization
  9. additionfrom a mixture of DCM and hexanes

Sources & evidence

ORD record
ord-ba0e230ea8694e0b88a891953931894f
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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