Trifluoroacetic acid → HCID 59614335, compound

HRID 409475Notes

Reaction equation

HRID 409475 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)[C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH2:41][CH3:42])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:39][C:37]([F:38])([F:40])[C:29]1[CH:28]=[C:27]([CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=1)[CH2:26][N:13]([C@H:11]1[CH2:10][C@@H:9]([CH2:41][CH3:42])[NH:8][CH2:12]1)[C:14]1[N:15]=[CH:16][C:17]([C:20]2[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=2)=[CH:18][N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 42633526HCID 42633526, compound

Product 1

HCID 59614335HCID 59614335, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,4S)-4-{(3,5-Bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.2 g, 2 mmol) in CH2Cl2 (20 mL) is added trifluoroacetic acid (7 mL) at room temperature. The reaction mixture is stirred at room temperature for 1.5 hours. The mixture is quenched with saturated aqueous NaHCO3 solution, then extracted with CH2Cl2. The combined organic layer is washed by saturated aqueous NaHCO3 solution, then dried over Na2SO4 and concentrated under reduced pressure to give (3,5-bis-trifluoromethyl-benzyl)-((3S,5R)-5-ethyl-pyrrolidin-3-yl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine as a yellow oil (1.01 g, quant.). ESI-MS m/z: 499 [M+1]+, Retention time 1.84 min (condition A).

Workup

  1. customThe mixture is quenched with saturated aqueous NaHCO3 solution
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layer is washed by saturated aqueous NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45cafba5e37e448d804e5f837070ff6f
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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