Ethanamine, 2,2,2-trifluoro- → N-(2-hydroxyethyl)-2-(2-(4-((2,2,2-trifluoroethylamino)methyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162781Notes

Reaction equation

HRID 1162781 reaction equation
[CH:1]([C:3]1[C:4]([C:27]([F:30])([F:29])[F:28])=[N:5][N:6]([CH2:8][C:9]([NH:11][C:12]2[S:16][C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[C:13]=2[C:21]([NH:23][CH2:24][CH2:25][OH:26])=[O:22])=[O:10])[CH:7]=1)=O.[F:31][C:32]([F:36])([F:35])[CH2:33][NH2:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(Cl)Cl>[OH:26][CH2:25][CH2:24][NH:23][C:21]([C:13]1[C:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:15]=2[S:16][C:12]=1[NH:11][C:9](=[O:10])[CH2:8][N:6]1[CH:7]=[C:3]([CH2:1][NH:34][CH2:33][C:32]([F:36])([F:35])[F:31])[C:4]([C:27]([F:29])([F:30])[F:28])=[N:5]1)=[O:22]

Participants

6

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 5049666Sodium triacetoxyborohydrideHCID 595204812-(2-(4-Formyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

Product 1

HCID 59520490N-(2-hydroxyethyl)-2-(2-(4-((2,2,2-trifluoroethylamino)methyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideYield 29.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(2-(4-Formyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (30 mg, 0.068 mmol), 2,2,2-trifluoroethylamine (19.8 mg, 0.20 mmol) and DCM (1 mL) were treated with acetic acid (5 drops) and sodium triacetoxyborohydride (58 mg, 0.272 mmol) and the mixture stirred at RT overnight. The sample was concentrated and re-dissolved in dimethylsulfoxide (1 mL), filtered and purified by preparative LCMS followed by additional purification by SCX ion exchange chromatography to yield the title compound (10 mg, 0.02 mmol, 29%).

Workup

  1. concentrationThe sample was concentrated
  2. dissolutionre-dissolved in dimethylsulfoxide (1 mL)
  3. filtrationfiltered
  4. custompurified by preparative LCMS
  5. customfollowed by additional purification by SCX ion exchange chromatography

Sources & evidence

ORD record
ord-cacd5eb24d6749438e20f411043124bd
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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