Trifluoroacetic acid → HCID 178456268, compound

HRID 1864782Notes

Reaction equation

HRID 1864782 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:62]=[CH:61][C:12]([C:13]([N:15]([CH2:25][C:26]2[CH:31]=[C:30]([C:32]3[CH:59]=[CH:58][C:35]4[N:36](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:37]=[N:38][C:34]=4[CH:33]=3)[CH:29]=[CH:28][C:27]=2[F:60])[CH:16]2[CH2:21][CH2:20][N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]2)=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH:36]1[C:35]2[CH:58]=[CH:59][C:32]([C:30]3[CH:29]=[CH:28][C:27]([F:60])=[C:26]([CH:31]=3)[CH2:25][N:15]([CH:16]3[CH2:21][CH2:20][N:19]([CH:22]([CH3:23])[CH3:24])[CH2:18][CH2:17]3)[C:13](=[O:14])[C:12]3[CH:11]=[CH:10][C:9]([F:8])=[CH:62][CH:61]=3)=[CH:33][C:34]=2[N:38]=[N:37]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 10340Sodium CarbonateHCID 68746443HCID 68746443, compound

Product 1

HCID 178456268HCID 178456268, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (TFA, 0.25 mL) was added to a solution of 4-fluoro-N-[2-fluoro-5-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-N-(1-isopropyl-piperidin-4-yl)-benzamide (18 mg, 0.024 mmol) in 1 mL of dichloromethane and the resulting mixture stirred at ambient temperature for 3 h, when an additional 0.5 mL of TFA was added. This was stirred overnight and then the mixture was neutralized by the 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 6.5 mg of product. LC/MS: Retention time, 2.25 min; (M+H)=490.

Workup

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

Sources & evidence

ORD record
ord-6362534744ab4cca8de6cf0cf17b9b33
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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