Trifluoroacetic acid → HCID 86603008, compound

HRID 735447Notes

Reaction equation

HRID 735447 reaction equation
[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][CH2:23][C@H:22]([NH:25]C(=O)OC(C)(C)C)[CH2:21]3)=[CH:16][CH:15]=2)=[C:12]2[C:7]([C:8]([C:33]([F:36])([F:35])[F:34])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][CH2:23][C@H:22]([NH2:25])[CH2:21]3)=[CH:16][CH:15]=2)=[C:12]2[C:7]([C:8]([C:33]([F:36])([F:34])[F:35])=[CH:9][CH:10]=[CH:11]2)=[N:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86603009HCID 86603009, compound

Product 1

HCID 86603008HCID 86603008, compoundYield 767.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl ((3S)-1-{4-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}pyrrolidin-3-yl)carbamate (0.05 g, 0.085 mmol) in 1 mL CH2Cl2 was treated with 0.1 mL of trifluoroacetic acid and stirred at ambient temperature overnight. Then the reaction mixture was partitioned with extra CH2Cl2 and saturated NaHCO3. The organic phase was isolated and dried (Na2SO4). The sovent was evaporated and the residue treated with excess HCl in diethyl ether. The solids were collected and dried to give 0.32 g of the title compound as the HCl salt.

Workup

  1. customThen the reaction mixture was partitioned with extra CH2Cl2 and saturated NaHCO3
  2. customThe organic phase was isolated
  3. dry with materialdried (Na2SO4)
  4. customThe sovent was evaporated
  5. additionthe residue treated with excess HCl in diethyl ether
  6. customThe solids were collected
  7. customdried

Sources & evidence

ORD record
ord-ca84a120de164afc809b1bff3073b2d6
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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