Trifluoroacetic acid → HCID 178519629, compound

HRID 1864784Notes

Reaction equation

HRID 1864784 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([N:11]2[CH2:16][CH2:15][CH:14]([N:17]([CH2:27][C:28]3[CH:33]=[C:32]([C:34]4[CH:61]=[CH:60][C:37]5[N:38](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[N:39]=[N:40][C:36]=5[CH:35]=4)[CH:31]=[CH:30][C:29]=3[F:62])[C:18](=[O:26])[C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)[CH2:10][CH2:9]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH:38]1[C:37]2[CH:60]=[CH:61][C:34]([C:32]3[CH:31]=[CH:30][C:29]([F:62])=[C:28]([CH:33]=3)[CH2:27][N:17]([CH:14]3[CH2:13][CH2:12][N:11]([CH:8]4[CH2:10][CH2:9]4)[CH2:16][CH2:15]3)[C:18](=[O:26])[C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)=[CH:35][C:36]=2[N:40]=[N:39]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 68750968HCID 68750968, compound

Product 1

HCID 178519629HCID 178519629, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (TFA, 1 mL) was added to a solution of N-(1-cyclopropyl-piperidin-4-yl)-4-fluoro-N-[2-fluoro-5-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-benzamide (14 mg, 0.019 mmol) in 1 mL of dichloromethane and the resulting mixture stirred at ambient temperature overnight and then the mixture was neutralized by careful addition of 1M sodium carbonate. The layers were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered, and the volatiles were removed in vacuo to leave the crude product. Chromatography (elution with methanol/dichloromethane) provided 9 mg of the title compound. LC/MS: Retention time, 2.22 min; (M+H)=488.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles were removed in vacuo
  6. customto leave the crude product
  7. washChromatography (elution with methanol/dichloromethane)

Sources & evidence

ORD record
ord-13fad5059d26471bab65ec2735d50cab
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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