Trifluoroacetic acid → HCID 70984185, compound

HRID 403359Notes

Reaction equation

HRID 403359 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C@H:20]2[C:26]3[N:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[S:29][C:25]=3[C@@H:24]([NH:34]C(OC(C)(C)C)=O)[C@H:23]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:43]=3[F:49])[CH2:22][CH2:21]2)=[O:18])[CH2:13][CH2:12]1.FC(F)(F)C(O)=O>C(Cl)Cl>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C@H:20]2[C:26]3[N:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[S:29][C:25]=3[C@@H:24]([NH2:34])[C@H:23]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:43]=3[F:49])[CH2:22][CH2:21]2)=[O:18])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70984156HCID 70984156, compound

Product 1

HCID 70984185HCID 70984185, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4R,7S,8S)-8-(tert-butoxycarbonylamino)-7-(2,3-difluorophenyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-4-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (3.5 mg, 4.94 μmol) in methylene chloride (2 mL) was treated with trifluoroacetic acid (0.5 mL, 6.49 mmol) at rt. The reaction was stirred for 2 h. The solvent was removed under vacuum and the crude product was partitioned between sodium bicarbonate(sat.) and ethyl acetate. The organic layer was separated, dried (sodium sulfate), filtered and concentrated in vacuo. Flash chromatography, eluting with methanol in methylene chloride from 0 to 10% gave the desired product (2.7 mg, 90%) as a white solid: LCMS (M+Na=631.04).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude product was partitioned between sodium bicarbonate(sat.) and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash chromatography, eluting with methanol in methylene chloride from 0 to 10%

Sources & evidence

ORD record
ord-84eb3116d0a447b0a4ad5286226bf366
Source dataset
uspto-grants-2014_06
Patent number
US08748429B2

Reaction notes

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