Chlorosulfonic acid → HCID 69314314, compound

HRID 2117744Notes

Reaction equation

HRID 2117744 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([NH2:31])[CH2:30][CH2:29]1>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:31][CH:28]4[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

6

Reactant 3

HCID 24638Chlorosulfonic acidHCID 69828CyclopropylamineHCID 113922232-Anilino-4-(1-methyl-2-isopropylimidazol-5-yl)pyrimidine

Product 1

HCID 69314314HCID 69314314, compoundYield 92%

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 cyclopropylamine (570 μl, 8.1 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 (205 mg, 92%) as a solid. NMR: 0.30 (m, 2H), 0.45 (m, 2H), 1.24 (d, 6H), 2.19 (m, 1H), 3.17 (m, 1H), 4.01 (s, 3H), 7.19 (d, 1H), 7.70 (d, 2H), 7.92 (d, 2H), 8.02 (m, 1H), 8.50 (d, 1H), 9.90 (brs, 1H); m/z 413.

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-520c25f9f33f4ea99c34843ac2ce9088
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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