Diethylmethylamine → 4-(1-Methyl-2-isopropylimidazol-5-yl)-2-{4-[N-(cyclobutyl)sulphamoyl]anilino}pyrimidine

HRID 2117743Notes

Reaction equation

HRID 2117743 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH3:24])[C:22]([CH:25]([CH3:27])[CH3:26])=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:28]1([NH2:32])[CH2:31][CH2:30][CH2:29]1.C(N(CC)C)C>S(Cl)(Cl)=O.CO>[CH3:24][N:23]1[C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:6][C:7]3[CH:12]=[CH:11][C:10]([S:2](=[O:5])(=[O:3])[NH:32][CH:28]4[CH2:31][CH2:30][CH2:29]4)=[CH:9][CH:8]=3)[N:18]=2)=[CH:20][N:21]=[C:22]1[CH:25]([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 12022DiethylmethylamineHCID 24638Chlorosulfonic acidHCID 75645CyclobutylamineHCID 11392223HCID 11392223, compound

Product 1

HCID 102879504-(1-Methyl-2-isopropylimidazol-5-yl)-2-{4-[N-(cyclobutyl)sulphamoyl]anilino}pyrimidineYield 65.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulphonic acid (150 μl, 2.16 mmol) was added dropwise to solution of 2-anilino-4-(1-methyl-2-isopropylimidazol-5-yl)pyrimidine (Method 71; 158 mg, 0.54 mmol) in thionyl chloride (3 ml) cooled at 0° C. and the mixture stirred at 0° C. for 10 minutes then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the residue was dried under high vacuum (<2 mmHg) for 1 hour. The resulting solid was placed under nitrogen and a solution of cyclobutylamine (100 μl, 1.08 mmol) and diethylmethylamine (1 ml, 15 mmol) in MeOH (3 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. Trituration with water results in a solid which was washed water (3×20 ml) collected by filtration and dried under vacuum at 60° C. to yield the title compound (151 mg, 65%) as a solid. NMR: 1.24 (d, 6H), 1.45 (m, 2H), 1.70 (m, 2H), 1.90 (m, 2H), 3.17 (m, 1H), 3.58 (m, 1H), 3.98 (s, 3H), 7.19 (d, 1H), 7.70 (m, 4H), 7.92 (d, 2H), 8.41 (d, 1H), 9.90 (brs, 1H); m/z 427.

Workup

  1. temperaturethen heated at 90° C. for 90 minutes
  2. customThe volatiles were removed by evaporation
  3. customthe residue was dried under high vacuum (<2 mmHg) for 1 hour
  4. stirringThe mixture was stirred for 30 minutes
  5. customthe volatiles were evaporated in vacuo
  6. customTrituration with water results in a solid which
  7. washwas washed water (3×20 ml)
  8. filtrationcollected by filtration
  9. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-4446ecdae1754881ab30d087d904bc34
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

Loading…