Trifluoroacetic acid → 3-[4-(1-aminocyclopropyl)phenyl]propynoic acid-(4'-chlorobiphenyl-4-yl)amide Trifluoroacetate

HRID 735021Notes

Reaction equation

HRID 735021 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:42])[C:23]#[C:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4([NH:34]C(OC(C)(C)C)=O)[CH2:33][CH2:32]4)=[CH:27][CH:26]=3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:42])[C:23]#[C:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4([NH2:34])[CH2:32][CH2:33]4)=[CH:27][CH:26]=3)=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68816272HCID 68816272, compound

Product 1

HCID 688198803-[4-(1-aminocyclopropyl)phenyl]propynoic acid-(4'-chlorobiphenyl-4-yl)amide Trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 mL (12.92 mmol) of trifluoroacetic acid is added to a solution of 0.24 g (0.49 mmol) of 3-[4-(1-tert-butoxycarbonylaminocyclopropyl)phenyl]propynoic acid-(4′-chlorobiphenyl-4-yl)amide in 20 mL dichloromethane and stirred for 24 hours. Then the solvent is eliminated by rotary evaporation and the residue is combined with toluene and again subjected to rotary evaporation. This residue is then triturated with dichloromethane, suction filtered and dried in the air. Yield: 0.22 g (89% of theory); C24H19ClN2O*C2HF3O2 (M=500.90); calc.: molecular ion peak (M+H)+: 387 (Cl); found: molecular ion peak (M+H)+: 387 (Cl); melting point: 160° C.-164° C.

Workup

  1. customThen the solvent is eliminated by rotary evaporation
  2. customagain subjected to rotary evaporation
  3. customThis residue is then triturated with dichloromethane, suction
  4. filtrationfiltered
  5. customdried in the air

Sources & evidence

ORD record
ord-7cb56a56b8b74a6f8a74a5f55b8cb919
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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