Trifluoroacetic acid → HCID 178465849, compound

HRID 2182374Notes

Reaction equation

HRID 2182374 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:30])=[CH:6][C:7]2[N:11]=[C:10]([C:12]3[C:16]([NH:17][C:18]([CH:20]4[CH2:22][CH2:21]4)=[O:19])=[CH:15][N:14](C4CCCCO4)[N:13]=3)[NH:9][C:8]=2[CH:29]=1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]1[C:5]([F:30])=[CH:6][C:7]2[N:11]=[C:10]([C:12]3[C:16]([NH:17][C:18]([CH:20]4[CH2:21][CH2:22]4)=[O:19])=[CH:15][NH:14][N:13]=3)[NH:9][C:8]=2[CH:29]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178465848HCID 178465848, compound

Product 1

HCID 178465849HCID 178465849, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cyclopropanecarboxylic acid [3-(6-ethoxy-5-fluoro-1H-benzimidazol-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]amide [90 mg, Reference Example 48(d)] in a 1/1 mixture of trifluoroacetic acid and dichloromethane (30 mL) was stirred for 5 hours and then evaporated. The residue was mixed with ethyl acetate (30 mL) and aqueous sodium bicarbonate (30 mL). The organic layer was evaporated to give cyclopropanecarboxylic acid [3-(6-ethoxy-5-fluoro-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]amide (44 mg). LC-MS (Method E): RT=2.34 minutes, 330 (M+H)+. (b) Tetrahydropyran-4-carboxylic acid [3-(6-ethoxy-5-fluoro-1H-benzimidazol-2-yl)-1H-pyrazole-4-yl]amide

Workup

  1. customevaporated
  2. additionThe residue was mixed with ethyl acetate (30 mL) and aqueous sodium bicarbonate (30 mL)
  3. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-79c2435d552147c0976a2b6e4b157f1a
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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