Diisopropylethylamine → N-[2-(benzylthio)-3,3-dimethoxypropyl]-4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide

HRID 1994775Notes

Reaction equation

HRID 1994775 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21](O)=[O:22])[NH:6]2.[CH2:24]([S:31][CH:32]([CH:35]([O:38][CH3:39])[O:36][CH3:37])[CH2:33][NH2:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([S:31][CH:32]([CH:35]([O:36][CH3:37])[O:38][CH3:39])[CH2:33][NH:34][C:21]([C:5]1[NH:6][C:7]2[C:3]([CH:4]=1)=[C:2]([CH3:1])[CH:10]=[CH:9][C:8]=2[N:11]([CH3:20])[S:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:14])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 574759902-(Benzylthio)-3,3-dimethoxypropan-1-amineHCID 574760074-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid

Product 1

HCID 59135744N-[2-(benzylthio)-3,3-dimethoxypropyl]-4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamideYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (3.0 g), 2-(benzylthio)-3,3-dimethoxypropan-1-amine (2.4 g), N-ethyldiisopropylamine (3.7 mL) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (4.2 g) in N,N-dimethylformamide (40 mL) was stirred at room temperature for 8 hr. The reaction solution was diluted with ethyl acetate, washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:3-3:2) to give the title compound (4.75 g, yield: 97%) as a pale-yellow oil. MS: 542 (MH+).

Workup

  1. washwashed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c352a71797a4ea8acac4c311932a4ea
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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