N,N-Dimethylethylenediamine → N-[2-(Dimethylamino)ethyl]-2-({[3-(Trifluoromethyl)-4,5,6,7-Tetrahydro-1h-Indazol-1-Yl]acetyl}amino)-4,5,6,7-Tetrahydro-1-Benzothiophene-3-Carboxamide

HRID 1162739Notes

Reaction equation

HRID 1162739 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([CH2:12][C:13]([NH:15][C:16]2[S:20][C:19]3[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=3[C:17]=2[C:25](O)=[O:26])=[O:14])[N:4]=1.[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH2:34].C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH:34][C:25]([C:17]1[C:18]2[CH2:24][CH2:23][CH2:22][CH2:21][C:19]=2[S:20][C:16]=1[NH:15][C:13](=[O:14])[CH2:12][N:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:3]([C:2]([F:29])([F:28])[F:1])=[N:4]1)=[O:26]

Participants

6

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 595204832-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid

Product 1

HCID 46870035N-[2-(Dimethylamino)ethyl]-2-({[3-(Trifluoromethyl)-4,5,6,7-Tetrahydro-1h-Indazol-1-Yl]acetyl}amino)-4,5,6,7-Tetrahydro-1-Benzothiophene-3-Carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (50 mg, 0.117 mmol) was dissolved in a solution of DCM (2 mL) and DMF (0.4 mL). O-(7-azabenzotriazol-1-yl)-N,N′,N′,N′-tetramethyluronium hexafluorophosphate (54 mg, 0.141 mmol) was added, followed by N,N-dimethylethylenediamine (15.5 μL, 0.141 mmol) and N,N-diisopropylethylamine (24.6 μL, 0.141 mmol). The resultant mixture was stirred at RT overnight. The solvent was removed under reduced pressure, and the residue obtained purified by preparative reverse phase HPLC, to afford the title compound, a colourless oil, as the TFA salt (52 mg, 0.084 mmol, 72%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue obtained
  3. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-08c3866ae8fb491b8068b0057208dd66
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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