Water → HCID 11666476, compound

HRID 1819717Notes

Reaction equation

HRID 1819717 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]1[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH:8]([C:19]([NH2:21])=[O:20])[NH:7]1)=[CH:17][CH:16]=[CH:15][CH:14]=3.C(N(CC)CC)C.O>CN(C=O)C>[CH3:1][S:2]([N:7]1[CH:8]([C:19]([NH2:21])=[O:20])[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH2:6]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11085189HCID 11085189, compound

Product 1

HCID 11666476HCID 11666476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methane sulphonyl chloride (0.18 ml, 2.4 mmol) 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 min at room temperature 30° C. The reaction mixture 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 extract was dried over Na2SO4 and concentrated over reduced pressure to give 2-[methanesulphonyl]-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=0.150 gm (25.60%). m.p.=234° C. Mass (FAB) m/z=294 (M+). IR (KBr cm−1): 3483, 3361, 1685, 1610, 1446, 1325, 1148, 756. H1NMR (200 MHz, CDCl3) δ 3.04 (s, 3H), δ3.20-3.63 (m, 2H), δ4.69-4.84 (m, 3H), δ6.96-7.15 (m, 3H), δ7.32-7.53 (m, 3H), δ10.89 (s, 1H). Molecular Formula=C13H15N3O3S.

Workup

  1. customat room temperature
  2. extractionextracted with chloroform (3×15 ml)
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated over reduced pressure
  5. customto give 2-[methanesulphonyl]-1,2,3,4
  6. custom-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

Sources & evidence

ORD record
ord-aeb68dac77e24fe5be334088131a19fb
Source dataset
uspto-grants-2009_10
Patent number
US07601838B2

Reaction notes

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