Hydrochloric Acid → HCID 69310879, compound

HRID 2375269Notes

Reaction equation

HRID 2375269 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH2:24][CH3:25])[CH:22]=[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:26]1([NH2:29])[CH2:28][CH2:27]1.Cl.CCOCC>S(Cl)(Cl)=O.CO>[CH2:24]([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:29][CH:26]4[CH2:28][CH2:27]4)=[CH:9][CH:8]=3)[N:18]=2)=[CH:20][N:21]=[CH:22]1)[CH3:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 24638Chlorosulfonic acidHCID 69828CyclopropylamineHCID 69309542HCID 69309542, compound

Product 1

HCID 69310879HCID 69310879, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulphonic acid (250 μl, 3.6 mmol) was added dropwise to solution of 2-anilino-4-(1-ethylimidazol-5-yl)pyrimidine (Method 32; 250 mg, 0.9 mmol) in thionyl chloride (5 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 (1 ml, 13.5 mmol) in MeOH (4ml) added. The mixture was stirred for 15 minutes and the volatiles were evaporated in vacuo. Water (20ml) was added and the resultant solid was washed with water (2×10 ml), ether (2×10 ml) and dried under vacuum at 60° C. for 18 hr. The resultant solid was dissolved in MeOH (4 ml) and treated with 1M HCl in ether (0.62 ml, 0.62 mmol). The solvent was evaporated in vacuo and the resultant solid triturated with ether, collected by filtration and dried under vacuum at 60° C. to yield the title compound (220 mg, 56%) as a golden solid. NMR: 0.34 (m, 2H), 0.52 (m, 2H), 1.52 (t, 3H), 2.21 (m, 1H), 4.77 (q, 2H), 7.43 (d, 1H), 7.74 (m, 3H), 7.93 (d, 2H), 8.54 (s, 1H), 8.72 (d, 1H), 9.41 (s, 1H), 10.20 (brs, 1H); m/z 385.

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 15 minutes
  5. customthe volatiles were evaporated in vacuo
  6. additionWater (20ml) was added
  7. washthe resultant solid was washed with water (2×10 ml), ether (2×10 ml)
  8. customdried under vacuum at 60° C. for 18 hr
  9. dissolutionThe resultant solid was dissolved in MeOH (4 ml)
  10. customThe solvent was evaporated in vacuo
  11. customthe resultant solid triturated with ether
  12. filtrationcollected by filtration
  13. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-69c170f9d1d6492f92c9c9c3e14b1b30
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

Loading…