Hydrochloric Acid → [2-(1,1-Dioxo-thiomorpholine-4-carbonyl)-1H-indol-5-yl]-(4-isopropyl-piperazin-1-yl)-methanone

HRID 1820319Notes

Reaction equation

HRID 1820319 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([OH:23])=O)=[CH:15]3)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH:47]1[CH2:52][CH2:51][S:50](=[O:54])(=[O:53])[CH2:49][CH2:48]1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[O:53]=[S:50]1(=[O:54])[CH2:51][CH2:52][N:47]([C:21]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:10]([N:7]2[CH2:8][CH2:9][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][CH2:6]2)=[O:11])=[CH:20][CH:19]=3)=[O:23])[CH2:48][CH2:49]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6484228Thiomorpholine 1,1-dioxideHCID 685341205-(4-isopropyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid

Product 1

HCID 68681206[2-(1,1-Dioxo-thiomorpholine-4-carbonyl)-1H-indol-5-yl]-(4-isopropyl-piperazin-1-yl)-methanoneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 0.20 g (0.57 mmol) 5-(4-isopropyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid 1:1 hydrochloride in 2 mL N,N-dimethylformamide, 0.19 g (0.60 mmol) O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (commercially available), 82 mg (0.60 mmol) thiomorpholine 1,1-dioxide (commercially available) and 0.58 mL (0.44 g, 3.4 mmol) N,N-diisopropylethylamine were added. After 1 h the solution was poured on saturated aqueous sodium bicarbonate solution, the phases were separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed three times with water followed by brine, dried over magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed twice on silica gel with dichloromethane:methanol:ammonia (12:1:0.1 v/v) as eluant to give 0.13 g (64%) of the desired compound as a light brown solid.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was flash-chromatographed twice on silica gel with dichloromethane:methanol:ammonia (12:1:0.1 v/v) as eluant

Sources & evidence

ORD record
ord-6ae102ff67cb433c9c76bc4cc0874934
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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