Hydrochloric Acid → HCID 14346756, compound

HRID 622598Notes

Reaction equation

HRID 622598 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[S:10]([NH2:13])(=[O:12])=[O:11])[CH:3]=[CH:2]1.C[O:15][C:16](=O)[NH:17][C:18]1[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([CH3:26])[N:19]=1.C[Al](C)C.Cl>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:25][O:24][C:22]1[CH:21]=[C:20]([CH3:26])[N:19]=[C:18]([NH:17][C:16]([NH:13][S:10]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[NH:1][CH:2]=[CH:3]3)(=[O:11])=[O:12])=[O:15])[N:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 143467551H-Indole-7-sulfonamideHCID 16682925Trimethylaluminum

Product 1

HCID 14346756HCID 14346756, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1H-indole-7-sulfonamide (1.0 g) and (4-methoxy-6-methylpyrimidin-2-yl)carbamic acid methyl ester (1.0 g) in methylene chloride (100 ml) was added trimethylaluminum (3.2 ml of a 2.0M 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 an oil. The oil was dissolved in ether from which it quickly crystallized to give pure product (TLC) (0.56 g, m.p. 207°-209° 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 an oil
  6. dissolutionThe oil was dissolved in ether from which it
  7. customquickly crystallized
  8. customto give pure product (TLC) (0.56 g, m.p. 207°-209° C.)

Sources & evidence

ORD record
ord-b61df04323384fe7ba233196ac2ec72e
Source dataset
uspto-grants-1988_09
Patent number
US04772313

Reaction notes

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