Hydrochloric Acid → HCID 14346756, compound

HRID 2119114Notes

Reaction equation

HRID 2119114 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 2.0 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 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-03ac3f95fdc24c54acb73ef9d5128fbc
Source dataset
uspto-grants-1987_07
Patent number
US04683000

Reaction notes

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