Trifluoroacetic acid → HCID 89963038, compound

HRID 337811Notes

Reaction equation

HRID 337811 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:4]=1[CH2:5][N:6]([C:32]1[CH:37]=[CH:36][N:35]=[CH:34][N:33]=1)[S:7]([C:10]1[C:11]([F:31])=[CH:12][C:13]([O:19][C@H:20]2[CH2:24][CH2:23][CH2:22][C@@H:21]2[C:25]2[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=2)=[C:14]([CH:18]=1)[C:15]([NH2:17])=O)(=[O:9])=[O:8].C(N(CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:15]([C:14]1[C:13]([O:19][C@H:20]2[CH2:24][CH2:23][CH2:22][C@@H:21]2[C:25]2[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=2)=[CH:12][C:11]([F:31])=[C:10]([S:7]([N:6]([CH2:5][C:4]2[CH:38]=[CH:39][C:40]([O:42][CH3:43])=[CH:41][C:3]=2[O:2][CH3:1])[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][N:33]=2)(=[O:8])=[O:9])[CH:18]=1)#[N:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 8471Triethylamine2×HCID 89963258HCID 89963258, compound

Product 1

HCID 89963038HCID 89963038, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the 5-{[(2,4-dimethoxybenzyl)(pyrimidin-4-yl)amino]sulfonyl}-4-fluoro-2-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzamide (64.3 mg, 0.107 mmol) prepared in Example 62c in dichloromethane (2.0 mL), triethylamine (41.0 μL, 0.300 mmol) and trifluoroacetic acid (21.0 μL, 0.150 mmol) were added with cooling on ice, and the reaction solution was stirred at room temperature for 2 hours. To the reaction solution, triethylamine (41.0 μL, 0.300 mmol) and trifluoroacetic acid (21.0 μL, 0.150 mmol) were added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was purified with silica gel chromatography (ethyl acetate) to yield the title compound (32.3 mg, 53%) as a colorless oil.

Workup

  1. temperaturewith cooling on ice
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. customThe reaction solution was purified with silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1c1582e80a9d4a37b921b1b6e5d15f0e
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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