p-Toluenesulfonic acid monohydrate → 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-N-(3-nitro-4-(4-oxo cyclohexylamino)phenylsulfonyl)benzamide

HRID 2040290Notes

Reaction equation

HRID 2040290 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22](=[O:61])[C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH2:34][CH2:33][N:32]([CH2:35][C:36]6[CH2:41][CH2:40][C:39]([CH3:43])([CH3:42])[CH2:38][C:37]=6[C:44]6[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=6)[CH2:31][CH2:30]5)=[CH:25][C:24]=4[O:51][C:52]4[CH:53]=[C:54]5[CH:60]=[CH:59][NH:58][C:55]5=[N:56][CH:57]=4)(=[O:20])=[O:19])=[CH:14][C:13]=3[N+:62]([O-:64])=[O:63])[CH2:7][CH2:6]2)[O:4]CC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O.ClCCl>[NH:58]1[C:55]2=[N:56][CH:57]=[C:52]([O:51][C:24]3[CH:25]=[C:26]([N:29]4[CH2:30][CH2:31][N:32]([CH2:35][C:36]5[CH2:41][CH2:40][C:39]([CH3:43])([CH3:42])[CH2:38][C:37]=5[C:44]5[CH:45]=[CH:46][C:47]([Cl:50])=[CH:48][CH:49]=5)[CH2:33][CH2:34]4)[CH:27]=[CH:28][C:23]=3[C:22]([NH:21][S:18]([C:15]3[CH:16]=[CH:17][C:12]([NH:11][CH:8]4[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]4)=[C:13]([N+:62]([O-:64])=[O:63])[CH:14]=3)(=[O:20])=[O:19])=[O:61])[CH:53]=[C:54]2[CH:60]=[CH:59]1

Participants

6

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 56591433n-(4-(1,4-Dioxaspiro[4.5]decan-8-ylamino)-3-nitrophenylsulfonyl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzamide

Product 1

HCID 671271112-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-N-(3-nitro-4-(4-oxo cyclohexylamino)phenylsulfonyl)benzamide

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of EXAMPLE 340B (386 mg) in acetone (10 mL) and water (5 mL) was added para-toluenesulfonic acid monohydrate (50 mg). The mixture was stirred at 120° C. in a Biotage Initiator microwave reactor for 30 minutes. The mixture was diluted with dichloromethane (300 mL) and washed with aqueous NaHCO3, water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the title compound.

Workup

  1. washwashed with aqueous NaHCO3, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-386c00badf0f4de18448b6364fa629b4
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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