Trifluoroacetic acid → HCID 86300985, compound

HRID 1500823Notes

Reaction equation

HRID 1500823 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:19]3[CH:20]=[C:21]([NH:25][C:26](=[O:29])[CH:27]=[CH2:28])[CH:22]=[CH:23][CH:24]=3)[N:17]=2)[N:12](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:11]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:19]3[CH:20]=[C:21]([NH:25][C:26](=[O:29])[CH:27]=[CH2:28])[CH:22]=[CH:23][CH:24]=3)[N:17]=2)[NH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117652657HCID 117652657, compound

Product 1

HCID 86300985HCID 86300985, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

A solution of compound 13 (90 mg, 1.449 mmol) in chloroform was added trifluoroacetic acid. The reaction was stirred overnight at 45° C., distilled off TFA and diluted with water and pH was adjusted to 9-10 with 1M NaOH solution at 20-25° C. The aqueous layer was extracted with dichloromethane (25 mL) twice. The organic layer was dried over sodium sulphate, filtered and concentrated to get the crude. The resulting oil was purified via silica gel chromatography using gradient of 50% Ethyl acetate in hexane to afford brown colour solid Compound 14. MS-ES+379.41, 1H NMR (400 MHz, DMSO-D6-d6) 14: 11.36 (d, 1H), 10.40 (d, 1H), 8.89 (d, 1H), 8.54 (d, 1H), 8.38 (d, 1H), 7.94 (d, 2H), 7.55 (d, 2H), 7.43 (d, 2H), 7.13 (d, 2H), 6.56 (d, 1H), 6.36 (d,1H), 5.83 (d, 1H), 5.31 (d, 1H).

Workup

  1. distillationdistilled off TFA
  2. additiondiluted with water and pH
  3. customwas adjusted to 9-10 with 1M NaOH solution at 20-25° C
  4. extractionThe aqueous layer was extracted with dichloromethane (25 mL) twice
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto get the crude
  9. customThe resulting oil was purified via silica gel chromatography

Sources & evidence

ORD record
ord-a77cf951ded54d87a62d3820a61a6bc6
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

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