Trifluoroacetic acid → HCID 178525663, compound

HRID 1615230Notes

Reaction equation

HRID 1615230 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[C:11]3/[C:12](=[O:28])[NH:13][C:14]4[C:19]/3=[CH:18][C:17]([NH:20]C(=O)OC(C)(C)C)=[CH:16][CH:15]=4)[CH:8]=2)[CH:3]=[N:2]1.[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30]>C(Cl)Cl>[F:32][C:31]([F:34])([F:33])[C:29]([O-:35])=[O:30].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[C:11]3/[C:12](=[O:28])[NH:13][C:14]4[C:19]/3=[CH:18][C:17]([NH3+:20])=[CH:16][CH:15]=4)[CH:8]=2)[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452631HCID 178452631, compound

Product 1

HCID 178525663HCID 178525663, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (E)-tert-butyl 3-((1H-indazol-6-yl)methylene)-2-oxoindolin-5-ylcarbamate (15 mg, 0.040 mmol) in CH2Cl2 (2 mL) was added TFA (0.1 mL). After 1.5 hrs the solvent was removed and the product precipitated with ether and filtered washing with ether to give 9 mg, 56% of the title compound as a brown solid. 1H NMR (400 MHz, d6-DMSO) δ 13.41 (s, 1H), 10.79 (s, 1H), 9.25-8.90 (bs, 3H), 9.01 (s, 1H), 8.14 (s, 1H), 8.00-7.96 (m, 2H), 7.82 (d, J=8.5 Hz, 1H), 7.56 (s, 1H), 7.09-7.07 (m, 1H), 6.86 (d, J=8.1 Hz, 1H); MS ESI 277.0 [M]+, calcd for [C16H13N4O]+ 277.11.

Workup

  1. customAfter 1.5 hrs the solvent was removed
  2. customthe product precipitated with ether
  3. filtrationfiltered
  4. washwashing with ether

Sources & evidence

ORD record
ord-cf2cf0713bad41da8943b0e492300b45
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…