Water → HCID 68496251, compound

HRID 1038759Notes

Reaction equation

HRID 1038759 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:17]([CH3:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([O:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][N:27]=2)=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:34][C:35]1[CH:36]=[C:37]([S:42](Cl)(=[O:44])=[O:43])[CH:38]=[CH:39][C:40]=1[Cl:41].N1C=CC=CC=1.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[N:17]([CH3:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([O:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][S:42]([C:37]4[CH:38]=[CH:39][C:40]([Cl:41])=[C:35]([Cl:34])[CH:36]=4)(=[O:44])=[O:43])=[CH:28][N:27]=2)=[CH:20][CH:19]=3)=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 68496054HCID 68496054, compound

Product 1

HCID 68496251HCID 68496251, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-[5-(5-aminopyridin-2-yloxy)-1-methyl-1H-indole-2-carbonyl]piperazine-1-carboxylic acid tert-butyl ester (4.69 g, 10.4 mmol) in THF (250 mL) was ice cooled, then 3,4-dichlorobenzenesulfonyl chloride (3.7 g, 15.1 mmol) and pyridine (1.51 mL, 18.7 mmol) were added to the solution. The resulting mixture was stirred for 17 hours while gradually warming up to room temperature. Water was added to the mixture, and the aqueous layer was extracted with AcOEt. The extract was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=40:1) to afford 5.26 g of the title compound as a pale yellow powder.

Workup

  1. temperaturecooled
  2. extractionthe aqueous layer was extracted with AcOEt
  3. washThe extract was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=40:1)

Sources & evidence

ORD record
ord-d635d4212f924947930d7244f70a3c3b
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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