Water → HCID 11531111, compound

HRID 1819716Notes

Reaction equation

HRID 1819716 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:13]1[C:18]2[NH:19][C:20]3[C:25]([C:17]=2[CH2:16][CH:15]([C:26]([NH2:28])=[O:27])[NH:14]1)=[CH:24][CH:23]=[CH:22][CH:21]=3.C(N(CC)CC)C.O>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:14]2[CH:15]([C:26]([NH2:28])=[O:27])[CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][C:18]=3[CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11085189HCID 11085189, compound

Product 1

HCID 11531111HCID 11531111, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

4-methoxy benzene sulphonyl chloride (495 gm, 2.4 mmol) in dry acetone (5 ml) was added to a stirred solution of dl 1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-amide (0.430 gm, 1.0 mmol) and dry triethylamine (0.56 ml, 4.0 mmol) in dry DMF (5 ml) during 15 min and was allowed to stirr for 8 hrs. at room temperature (32° C.). Water was added to the reaction mixture and triturated to give 2-[4-methoxybenzenesulfonyl]-1,2,3,4,-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid amide, which was purified by column chromatography over silica gel using 2% methanol chloroform as eluent. Yield=0.480 gm, (62.34%). m.p.=178-180° C.

Workup

  1. customat room temperature
  2. custom(32° C.)
  3. customtriturated

Sources & evidence

ORD record
ord-55ce4a929a5c46029fd69b02e6024732
Source dataset
uspto-grants-2009_10
Patent number
US07601838B2

Reaction notes

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