4-amino-N-(2-methoxyethyl)benzene-1-sulfonamide → HCID 10110828, compound

HRID 1071937Notes

Reaction equation

HRID 1071937 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[C:5]([C:12]#[N:13])=[CH:4][N:3]=1.[CH3:14][O:15][CH2:16][CH2:17][NH:18][S:19]([C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>CC(O)CC>[C:12]([C:5]1[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[N:7][C:2]([NH:26][C:25]2[CH:27]=[CH:28][C:22]([S:19](=[O:21])(=[O:20])[NH:18][CH2:17][CH2:16][O:15][CH3:14])=[CH:23][CH:24]=2)=[N:3][CH:4]=1)#[N:13]

Participants

4

Reactant 2

HCID 167819184-amino-N-(2-methoxyethyl)benzene-1-sulfonamideHCID 22390594HCID 22390594, compound

Product 1

HCID 10110828HCID 10110828, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent2×

Conditions

Temperature
90 °C

Procedure

2-Chloro-5-cyano-4-cyclopropylaminopyrimidine (Method 96; 295 mg, 1.28 mmol) was dissolved in hot 2-butanol (3 ml). A hot solution of 4-[N-(2-methoxyethyl)sulphamoyl]aniline (Method 5; 207 mg, 0.90 mmol) in 2-butanol (3 ml) was added and the reaction was stirred and heated at 90° C. for 1 hour. The reaction mixture was cooled and the volatiles evaporated to give a solid. The solid residue was triturated with hot ethyl acetate, cooled, and the resultant solid collected by filtration to give the title compound (270 mg, 77%). NMR: 0.68 (m, 2H), 0.80 (m, 2H), 2.88 (m, 3H), 3.14 (s, 3H), 3.28 (m, 2H), 7.48 (brs, 1H), 7.70 (d, 2H), 8.05 (d, 2H), 8.12 (brs, 1H) 8.41 (s, 1H), 10.31 (s, 1H); m/z: 389.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe volatiles evaporated
  3. customto give a solid
  4. customThe solid residue was triturated with hot ethyl acetate
  5. temperaturecooled
  6. filtrationthe resultant solid collected by filtration

Sources & evidence

ORD record
ord-66a55060a6414b15985b012386beee66
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

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