Trifluoroacetic acid → HCID 86300843, compound

HRID 1500822Notes

Reaction equation

HRID 1500822 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[C:19]4[C:14](=[N:15][CH:16]=[C:17]([C:20]5[CH:21]=[C:22]([NH:26][C:27](=[O:30])[CH:28]=[CH2:29])[CH:23]=[CH:24][CH:25]=5)[N:18]=4)[N:13](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[C:19]4[C:14](=[N:15][CH:16]=[C:17]([C:20]5[CH:21]=[C:22]([NH:26][C:27](=[O:30])[CH:28]=[CH2:29])[CH:23]=[CH:24][CH:25]=5)[N:18]=4)[NH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117652439HCID 117652439, compound

Product 1

HCID 86300843HCID 86300843, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

A solution of Compound 9 (20 mg, 0314 mmol) in chloroform was added trifluoro acetic acid. The reaction was stirred overnight at 45° C. The reaction was completely distilled and diluted with water, adjust the pH to 9-10 with 1 molar NaOH solution at 20-25° C. The aqueous layer was extracted with DCM (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:hexane afforded Compound 10. MS-ES +393.16; 1H NMR (400 MHz, DMSO-D6-d6) 10: 12.29 (d, 1H),11.17 (d, 1H), 10.39 (d,1H), 8.84 (d,1H), 8.54 (d,1H),7.94 (d, 2H),7.55 (d, 2H), 7.49 (d, 2H),7.26(d, 2H), 6.83 (d, 1H), 6.54 (d,1H), 6.36 (d, 1H) 5.81 (d, 1H), 4.45 (d, 3H).

Workup

  1. distillationThe reaction was completely distilled
  2. additiondiluted with water
  3. customat 20-25° C
  4. extractionThe aqueous layer was extracted with DCM (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-b1ae7220a64742519bc700c7dd265212
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

Loading…