Trifluoroacetic acid → HCID 178460022, compound

HRID 1500819Notes

Reaction equation

HRID 1500819 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[C:19]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])[CH:20]=[CH:21][CH:22]=4)[CH:16]=[C:11]3[C:10]([CH3:28])=[N:9]2)=CC=1.FC(F)(F)C(O)=O.C(OCC)(=O)C>C(Cl)(Cl)Cl.CCCCCC>[CH3:28][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])[CH:20]=[CH:21][CH:22]=3)[CH:16]=2)[NH:8][N:9]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 68388524N-(3-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)acrylamide

Product 1

HCID 178460022HCID 178460022, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of Compound 3 (70 mg, 0.175 mmol) in chloroform (15 mL) was added trifluoroacetic acid (3 mL) and heated to 50° C. overnight. The reaction was evaporated and diluted with water; pH was adjusted to 8-10 with sodium carbonate solution. The aqueous phase was extracted with dichloromethane twice (2×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude, which was passed through 100-200 mesh silica gel eluting the EXAMPLE 1 at 60% ethyl acetate in hexane as pale yellow colour solid. MS-ES+ 277.9, 1H NMR (400 MHz, DMSO-D6-D6) 4: 13.29 (s, 1H), 10.29 (s, 1H), 8.74 (d, 1H), 8.40 (d, 1H), 8.03 (s, 1H), 7.69 (m, 1H), 7.43 (m, 2H), 6.44 (m, 1H), 6.26 (dd, 1H), 5.78 (dd, 1H), 2.55 (s, 3H).

Workup

  1. customThe reaction was evaporated
  2. additiondiluted with water
  3. extractionThe aqueous phase was extracted with dichloromethane twice (2×25 mL)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated
  6. customto get the crude, which

Sources & evidence

ORD record
ord-6f707de7d853461f8f748127fbb86b30
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

Loading…