Water → HCID 11553030, compound

HRID 1819719Notes

Reaction equation

HRID 1819719 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=[O:12])=[O:11].[CH2:14]1[C:19]2[NH:20][C:21]3[C:26]([C:18]=2[CH2:17][CH:16]([C:27]([NH2:29])=[O:28])[NH:15]1)=[CH:25][CH:24]=[CH:23][CH:22]=3.C(N(CC)CC)C.O>CC(C)=O.CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:15]1[CH:16]([C:27]([NH2:29])=[O:28])[CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]=2[CH2:14]1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 11085189HCID 11085189, compound

Product 1

HCID 11553030HCID 11553030, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

2,4,6trimethyl benzene sulphonyl chloride (0.524 gm, 2.4 mmol) in dry acetone was added to a stirred solution of dl 1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-amide (0.430 gm, 2.0 mmol) and dry triethylamine (0.56 ml, 4.0 mmol) in dry DMF (8 ml) during 15 and was allowed to stirr for 8 hrs. at room temperature. Water (20 ml) was added to the reaction mixture and extracted with chloroform (3×15 ml). The tract was dried over Na2SO4 and concentrated over reduced pressure to give 2-[2,4,6trimethylbenzenesulfonyl]-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=0.35 gm (44.08%) m.p.=212° C.: Mass (FAB) m/z=398 (M+). IR (KBr cm−1): 3394, 3299, 1668, 1596, 1455, 1324, 1155, 752. H1NMR (200 MHz, DMSO d6) δ 2.30 (s, 3H), δ2.56-2.74 (m, 7H), δ3.55-3.62 (d, 1H), δ4.49-4.70 (m, 3H), δ5.17 (s, 1H), δ5.49 (s, 1H), δ6.96-7.77 (m, 6H). Molecular Formula=C21H23N3O3S.

Workup

  1. customat room temperature
  2. extractionextracted with chloroform (3×15 ml)
  3. dry with materialThe tract was dried over Na2SO4
  4. concentrationconcentrated over reduced pressure

Sources & evidence

ORD record
ord-a2da235626424e9a9e51c9eef690b6c3
Source dataset
uspto-grants-2009_10
Patent number
US07601838B2

Reaction notes

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