Trifluoroacetic acid → HCID 178463221, compound

HRID 2053725Notes

Reaction equation

HRID 2053725 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=1.C1CCC(N=C=NC2CCCCC2)CC1.C(OC(=O)[NH:41][CH:42]1[C:50]2[C:45](=[CH:46][CH:47]=[C:48]([N:51]=[C:52]([NH:54][CH2:55][CH2:56][C:57]3[CH:62]=[CH:61][C:60]([F:63])=[CH:59][CH:58]=3)[CH3:53])[CH:49]=2)[CH2:44][CH2:43]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:63][C:60]1[CH:59]=[CH:58][C:57]([CH2:56][CH2:55][NH:54][C:52](=[N:51][C:48]2[CH:49]=[C:50]3[C:45]([CH2:44][CH2:43][C@H:42]3[NH:41][C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:2]([F:1])([F:19])[F:18])=[CH:14][CH:13]=3)=[O:17])=[CH:46][CH:47]=2)[CH3:53])=[CH:62][CH:61]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 10868DicyclohexylcarbodiimideHCID 27827142'-Trifluoromethyl (1,1'-biphenyl)-4-carboxylic acidHCID 178463227HCID 178463227, compound

Product 1

HCID 178463221HCID 178463221, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir a mixture of 2′-trifluoromethylbiphenyl-4-carboxylic acid (100 mg, 0.376 mmol), N-hydroxysuccinimmide (43 mg, 0.376 mmol) and DCC (77 mg, 0.376 mmol) in 15 mL of methylene chloride at rt for 2 h. Combine (6-(1-((4-fluorobenzyl)methylamino)ethylideneamino)indan-1-yl)carbamic acid tert-butyl ester (129 mg. 0.313 mmol) with TFA (2 mL) at 0° C. and stir for 2 hr. Evaporate TFA under reduced pressure. Dissolve the residue in methylene chloride and evaporate to dryness; repeat this three times. Add 5 mL of methylene chloride and 1 mL of triethylamine. Add this resulting solution to the above mixture and stir at rt for 12 h. Pour the mixture into methylene chloride, wash with water, dry with Na2SO4, and concentrate. Purify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2) to give 82 mg of the title compound as a white solid (47% yield).

Workup

  1. customevaporate to dryness
  2. additionAdd 5 mL of methylene chloride and 1 mL of triethylamine
  3. additionAdd this resulting solution to the above mixture
  4. stirringstir at rt for 12 h
  5. additionPour the mixture into methylene chloride
  6. washwash with water
  7. dry with materialdry with Na2SO4
  8. concentrationconcentrate
  9. customPurify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c36aff9b2e3248fa83eb4d93560f189e
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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