Trifluoroacetic acid → HCID 67002761, compound

HRID 2362666Notes

Reaction equation

HRID 2362666 reaction equation
[Cl:1][C:2]1[C:3]([C:39]2[S:43][C:42]([C:44]3([OH:48])[CH2:47][CH2:46][CH2:45]3)=[N:41][CH:40]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)[CH:15]=3)[N:8]([S:29]([C:32]3[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([C:39]2[S:43][C:42]([C:44]3([OH:48])[CH2:45][CH2:46][CH2:47]3)=[N:41][CH:40]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[CH:15]=3)[N:8]([S:29]([C:32]3[CH:33]=[CH:34][C:35]([CH3:36])=[CH:37][CH:38]=3)(=[O:31])=[O:30])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67003655HCID 67003655, compound

Product 1

HCID 67002761HCID 67002761, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(5-chloro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (Example 50A) (120 mg, 0.169 mmol) in dichloromethane (846 μl) was added trifluoroacetic acid (652 μl, 8.46 mmol). The reaction was stirred for 1 hour and was then concentrated to dryness. The residue was partitioned between ethyl acetate (5 mL) and saturated aqueous bicarbonate solution (1 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification. MS ESI(+) m/z 609.4 [M+H]+.

Workup

  1. concentrationwas then concentrated to dryness
  2. customThe residue was partitioned between ethyl acetate (5 mL) and saturated aqueous bicarbonate solution (1 mL)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e34cb6b249944fb0869c7098d6afcfd6
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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