Trifluoroacetic acid → HCID 67003382, compound

HRID 2362644Notes

Reaction equation

HRID 2362644 reaction equation
[Cl:1][C:2]1[C:3]([C:33]2[S:37][C:36]([C:38]3([O:42]CC4C=CC(OC)=CC=4)[CH2:41][O:40][CH2:39]3)=[N:35][CH:34]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[CH:15]=3)[N:8]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([C:33]2[S:37][C:36]([C:38]3([OH:42])[CH2:41][O:40][CH2:39]3)=[N:35][CH:34]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[CH:15]=3)[N:8]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=3)(=[O:25])=[O:24])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67003555HCID 67003555, compound

Product 1

HCID 67003382HCID 67003382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ambient solution of 5-(5-chloro-2-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(3-(4-methoxybenzyloxy)oxetan-3-yl)thiazole (Example 20B) (160 mg, 0.215 mmol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (2.5 mL, 32.4 mmol). The reaction was stirred for 0.5 hours and then concentrated to dryness under reduced pressure. 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. The residue was purified by flash chromatography on silica gel, eluting with 0 to 10% methanol in dichloromethane, to give the title compound. MS ESI(+) m/z 625.1 [M+H]+.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  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
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with 0 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-e5ff7aea933044e983f887982bb20154
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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