Trifluoroacetic acid → HCID 67002707, compound

HRID 2362634Notes

Reaction equation

HRID 2362634 reaction equation
[Cl:1][C:2]1[C:3]([C:34]2[S:38][C:37]([C:39]3([O:43]CC4C=CC(OC)=CC=4)[CH2:42][O:41][CH2:40]3)=[N:36][CH:35]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:23]=[CH:22][C:14]([CH2:15][N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)=[CH:13][CH:12]=3)[N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([C:34]2[S:38][C:37]([C:39]3([OH:43])[CH2:40][O:41][CH2:42]3)=[N:36][CH:35]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH2:15][N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)=[CH:22][CH:23]=3)[N:8]([S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67003360HCID 67003360, compound

Product 1

HCID 67002707HCID 67002707, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ambient solution of 4-(4-(5-chloro-4-(2-(3-(4-methoxybenzyloxy)oxetan-3-yl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)benzyl)morpholine (Example 11H) (130 mg, 0.172 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 was then concentrated to dryness under reduced pressure. The residue was partitioned between ethyl acetate (5 mL) and saturated aqueous bicarbonate solution (1 mL). The layers were separated, and 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 a gradient of 0 to 10% methanol in dichloromethane, to give the title compound. MS ESI(+) m/z 637.1 [M+H]+.

Workup

  1. concentrationwas then concentrated to dryness under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (5 mL) and saturated aqueous bicarbonate solution (1 mL)
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with a gradient of 0 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-81a69ff94a1245c3ad83b37258a9f0a7
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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