Water → HCID 67426693, compound

HRID 2235468Notes

Reaction equation

HRID 2235468 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2[CH:9]=[C:8]3[NH:11][C:12]([NH:14][CH3:15])=[N:13][C:7]3=[CH:6][C:5]=2[N:4]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:3]1=[O:21].[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.O>N1C=CC=CC=1>[CH3:22][C:2]1([CH3:1])[C:10]2[CH:9]=[C:8]3[N:11]([S:30]([C:27]4[CH:28]=[CH:29][C:24]([CH3:23])=[CH:25][CH:26]=4)(=[O:32])=[O:31])[C:12]([NH:14][CH3:15])=[N:13][C:7]3=[CH:6][C:5]=2[N:4]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:3]1=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 674266807,7-Dimethyl-2-methylamino-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Product 1

HCID 67426693HCID 67426693, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 7,7-dimethyl-2-methylamino-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (230 mg) in pyridine (6 ml) is added 4-methyl-benzenesulfonyl chloride (160 mg; 0.84 mmol) at 0° C. After addition the mixture is warmed to RT and stirred for 48 h. The reaction solution is dissolved with water and the aqueous layer is extracted with EtOAc. The combined organic layer is washed with hydrochloric acid (0.5 N) and brine, dried over Na2SO4 and concentrated in vacuo. The compound (135 mg) is obtained by flash chromatography on silica gel eluting with CH2Cl2/MeOH (40:1).

Workup

  1. additionAfter addition the mixture
  2. extractionthe aqueous layer is extracted with EtOAc
  3. washThe combined organic layer is washed with hydrochloric acid (0.5 N) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85ed162d2e02429baae3ecc4ca6ece89
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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