1,8-Diazabicyclo(5.4.0)undec-7-ene → N,N-Dimethyl-5-chloro-3-cyclohexyl-3-hydroxy-1-tosylindoline-2-carboxamide

HRID 1901807Notes

Reaction equation

HRID 1901807 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[N:16]([S:23]([C:26]2[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:17][C:18](=[O:22])[N:19]([CH3:21])[CH3:20])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:21][N:19]([CH3:20])[C:18]([CH:17]1[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)([OH:8])[C:9]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:15])[CH:14]=2)[N:16]1[S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:24])=[O:25])=[O:22]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 543616542-[N-(Tosyl)-N-(dimethylcarbamoylmethyl)amino]-5-chlorophenyl cyclohexyl ketone

Product 1

HCID 23368623N,N-Dimethyl-5-chloro-3-cyclohexyl-3-hydroxy-1-tosylindoline-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g of the product obtained in step C are treated with 950 mg of DBU in 10 ml of DCM for 24 hours at RT. The reaction medium is then chromatographed on silica using a DCM/AcOEt mixture (95/5, v/v) as the eluent to give the other isomer (cis isomer). It is recrystallized from isopropyl ether.

Workup

  1. customThe reaction medium is then chromatographed on silica using a DCM/AcOEt mixture (95/5
  2. customv/v) as the eluent to give the other isomer (cis isomer)
  3. customIt is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-f867118c7902485a9ffcf33f786e2d63
Source dataset
uspto-grants-1996_11
Patent number
US05578633

Reaction notes

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