Trifluoroacetic acid → HCID 9909603, compound

HRID 2301812Notes

Reaction equation

HRID 2301812 reaction equation
[C:1]([C:5]1[CH:38]=[CH:37][C:8]([C:9]([NH:11][C:12]2[CH:36]=[CH:35][CH:34]=[CH:33][C:13]=2[C:14]([NH:16][C:17]2[CH:25]=[C:24]3[C:20]([CH:21]=[N:22][N:23]3C(OC(C)(C)C)=O)=[CH:19][CH:18]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C1(OC)C=CC=CC=1.ClCCl>[C:1]([C:5]1[CH:38]=[CH:37][C:8]([C:9]([NH:11][C:12]2[CH:36]=[CH:35][CH:34]=[CH:33][C:13]=2[C:14]([NH:16][C:17]2[CH:25]=[C:24]3[C:20]([CH:21]=[N:22][NH:23]3)=[CH:19][CH:18]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12018609HCID 12018609, compound

Product 1

HCID 9909603HCID 9909603, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a stirring solution of 2-[(4-t-butylbenzoyl)amino]-N-(1-Boc-6-indazolyl)benzamide (200 mg, 0.39 mmol) in anisole (1 mL) and dichloromethane (10 mL) was added TFA (10 mL). After stirring for 30 min, the solvents were removed by rotary evaporation and the residue was partitioned between ethyl acetate and satd aq NaHCO3. The aqueous phase was removed and the organic phase was washed again with NaHCO3, followed by brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo to a very small volume, then diluted with ether and sonicated. The white precipitate was then filtered and dried in vacuo to give 124 mg (77%) of white solid.

Workup

  1. customthe solvents were removed by rotary evaporation
  2. customthe residue was partitioned between ethyl acetate
  3. customThe aqueous phase was removed
  4. washthe organic phase was washed again with NaHCO3
  5. dry with materialThe organic phase was then dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a very small volume
  8. additiondiluted with ether
  9. customsonicated
  10. filtrationThe white precipitate was then filtered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-6717ac5580504c878e0b43243a6fa8f2
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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