Water → HCID 11632718, compound

HRID 1819718Notes

Reaction equation

HRID 1819718 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[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>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([N:15]2[CH:16]([C:27]([NH2:29])=[O:28])[CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][C:19]=3[CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 11085189HCID 11085189, compound

Product 1

HCID 11632718HCID 11632718, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

3-nitro benzene sulphonyl chloride (0.53 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 min and was allowed to sir for 8 hrs. at room temperature. The reaction mixture was allowed to stirr for 8hrs. 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-[3-nitrobenzenesulfonyl]-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=0.400 gm (50%). m.p.=252° C. Mass (FAB) m/z=401 (M+). IR (KBr cm−1): 3459, 3378, 1692, 1618, 1528, 1353, 11173, 760. H1NMR (200MHz, CDCl3+DMSO d6): δ2.88 (m, 1H), δ3.33 (d, 1H), δ4.73 (d, 1H), δ4.93 (d, 1H), δ5.06 (d, 1H), δ6.41 (s, 1H), δ6.89-7.31 (m, 3H), δ7.63-7.71 (m, 3H), δ8.13-8.17 (d, 1H), δ8.30 (d, 1H), δ8.59 (d, 1H), δ 10.27 (s, 1H). Molecular Formula=C18H16N4O5S.

Workup

  1. customat room temperature
  2. waitto stirr for 8hrs
  3. customat room temperature
  4. extractionextracted with chloroform (3×15 ml)
  5. dry with materialThe extract was dried over Na2SO4
  6. concentrationconcentrated over reduced pressure

Sources & evidence

ORD record
ord-3768b4c8a9804dc6a9b9b3e1dae1ee6b
Source dataset
uspto-grants-2009_10
Patent number
US07601838B2

Reaction notes

Loading…