HCID 11298485, compound → 2-{4-[N-(2-Methoxyethy)sulphamoyl]anilino}-4-(2-propyn-1-yloxy)-5-cyanopyrimidine

HRID 495370Notes

Reaction equation

HRID 495370 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]#[CH:11])[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>[CH3:14][O:15][CH2:16][CH2:17][NH:18][S:19]([C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:2]2[N:7]=[C:6]([O:8][CH2:9][C:10]#[CH:11])[C:5]([C:12]#[N:13])=[CH:4][N:3]=2)=[CH:24][CH:23]=1)(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 11298485HCID 11298485, compoundHCID 167819184-amino-N-(2-methoxyethyl)benzene-1-sulfonamide

Product 1

HCID 98432022-{4-[N-(2-Methoxyethy)sulphamoyl]anilino}-4-(2-propyn-1-yloxy)-5-cyanopyrimidineYield 67%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

A solution of 2-chloro-4-(2-propyn-1-yloxy)-5-cyanopyrimidine (Method 17; 219 mg, 1.13 mmol) and 4[N-(2-methoxyethyl)sulphamoyl]aniline (Method 38; 130 mg, 0.56 mmol) in 2-butanol (8 ml) was stirred at 50° C. for 18 hours. Solvent was removed under reduced pressure and the product recrystallized from methanol to give the title compound (145 mg, 67%). NMR: 2.90 (q, 2H), 3.15 (s, 3H), 3.25 (m, 2H), 3.70 (s, 1H), 5.20 (s, 2H), 7.55 (t, 1H), 7.75 (d, 2H), 7.90 (d, 2H), 8.80 (s, 1H); m/z 387.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe product recrystallized from methanol

Sources & evidence

ORD record
ord-51def6ac00294012863627f126ec72da
Source dataset
uspto-grants-2005_09
Patent number
US06939872B2

Reaction notes

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