Hydrochloric Acid → 2,3-Dihydro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methyl-1H-indole-7-sulfonamide

HRID 2119112Notes

Reaction equation

HRID 2119112 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=2)[NH:3]1.C[O:16][C:17](=O)[NH:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([CH3:27])[N:20]=1.C[Al](C)C.Cl>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:26][O:25][C:23]1[CH:22]=[C:21]([CH3:27])[N:20]=[C:19]([NH:18][C:17]([NH:14][S:11]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[NH:3][CH:2]([CH3:1])[CH2:10]3)(=[O:13])=[O:12])=[O:16])[N:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 143467302,3-dihydro-2-methyl-1H-indole-7-sulfonamideHCID 16682925Trimethylaluminum

Product 1

HCID 143467312,3-Dihydro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methyl-1H-indole-7-sulfonamideYield 11.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dihydro-2-methyl-1H-indole-7-sulfonamide (1.0 g) and (4-methoxy-6-methylpyrimidin-2-yl)carbamic acid methyl ester (1.0 g) in methylene dichloride (100 ml) was added trimethylaluminum (3.0 ml of a 2.0 M solution in toluene). The mixture was heated at reflux for 18 hours under a nitrogen atmosphere. Work-up was achieved by careful addition of 100 ml of 1N HCl followed by separation of the organic layer. The methylene chloride was dried over MgSO4 and evaporated to dryness. The residue was chromatographed on a silica gel column to give the pure product (0.2 g, m.p. 175°-177° C.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours under a nitrogen atmosphere
  3. customfollowed by separation of the organic layer
  4. dry with materialThe methylene chloride was dried over MgSO4
  5. customevaporated to dryness
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-018833fdf64e429cab4537f79ffd197b
Source dataset
uspto-grants-1987_07
Patent number
US04683000

Reaction notes

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