Hydrochloric Acid → N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-pyridinyl)benzenesulfonamide

HRID 35493Notes

Reaction equation

HRID 35493 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:15])=[O:14].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([NH:27][C:28](=O)[O:29]C)[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:24]=[C:19]([O:18][CH3:17])[N:20]=[C:21]([NH:27][C:28]([NH:16][S:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)(=[O:14])=[O:15])=[O:29])[N:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13314628Methyl (4,6-dimethoxypyrimidin-2-yl)carbamateHCID 133705862-(Pyridin-2-yl)benzene-1-sulfonamideHCID 16682925Trimethylaluminum

Product 1

HCID 13370587N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-pyridinyl)benzenesulfonamideYield 42.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.2 g of the compound from Example 2 and 1.3 g of methyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate in 50 ml of methylene chloride was stirred under nitrogen and 3.4 ml of a 2N solution of trimethylaluminum in toluene was added. After heating at reflux for 4 days, the solution was cooled to 0°, 3 ml of 2N HCl (aq.) was added, the mixture was partitioned between methylene chloride and water. The organic layer was concentrated and the residue was chromatographed on silica gel to afford 0.9 g of the product, m.p. 175°-176°. NMR (DMSO-d6)δ: 3.8 (s, 6), 6.0 (s, 1), 7.2-8.3 (m).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 4 days
  3. temperaturethe solution was cooled to 0°
  4. customthe mixture was partitioned between methylene chloride and water
  5. concentrationThe organic layer was concentrated
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-6f6a11f8abbd447a875abbb5cda519ae
Source dataset
uspto-grants-1988_08
Patent number
US04767445

Reaction notes

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