Ammonium Chloride → [5-(4-Isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

HRID 1992452Notes

Reaction equation

HRID 1992452 reaction equation
Cl.[CH:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22](O)=[O:23])=[CH:16]3)=[O:12])[CH2:7][CH2:6]1)([CH3:4])[CH3:3].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH3:47][S:48]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)(=[O:50])=[O:49].C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>CN(C)C=O>[CH:2]([N:5]1[CH2:6][CH2:7][N:8]([C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22]([N:54]2[CH2:55][CH2:56][N:51]([S:48]([CH3:47])(=[O:50])=[O:49])[CH2:52][CH2:53]2)=[O:23])=[CH:16]3)=[O:12])[CH2:9][CH2:10]1)([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 7091611-(Methylsulfonyl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68534119HCID 68534119, compound

Product 1

HCID 68538245[5-(4-Isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanoneYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.70 g (4.8 mmol) 5-(4-isopropyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid hydrochloride in 17 mL N,N-dimethylformamide, were added 1.94 g (6.0 mmol) O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 1.0 g (6.0 mmol) 1-methylsulfonyl-piperazine and 4.1 mL (3.1 g, 24.0 mmol) N,N-diisopropylethylamine. After 2 h the solution was poured into 10% aqueous ammonium chloride solution, the phases were separated and the aqueous phase was extracted ten times with ethyl acetate. The combined organic layers were washed three times with water, brine, dried over magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed twice on silica gel with dichloromethane:methanol (9:1 v/v) as eluant to give 1.45 g (65%) of the desired compound as a light-brown foam. MS (ISP): 462.1 (M+H)+.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted ten times with ethyl acetate
  3. washThe combined organic layers were washed three times with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was flash-chromatographed twice on silica gel with dichloromethane:methanol (9:1 v/v) as eluant

Sources & evidence

ORD record
ord-13f9b5f4c0ce42308ab6e20586a75794
Source dataset
uspto-grants-2010_01
Patent number
US07648979B2

Reaction notes

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