Hydrochloric Acid → HCID 11396244, compound

HRID 2105186Notes

Reaction equation

HRID 2105186 reaction equation
O[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:15]=2)[N:3]=1.[NH2:25][C:26]1[CH:30]=[C:29]([CH:31]2[CH2:33][CH2:32]2)[NH:28][N:27]=1.Cl>P(Cl)(Cl)(Cl)=O.O1CCOCC1.CN1C(=O)CCC1>[CH:31]1([C:29]2[NH:28][N:27]=[C:26]([NH:25][C:2]3[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]4[CH2:13][CH2:12][CH2:11][CH:10]4[C:14]4[O:18][N:17]=[C:16]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=5)[CH:15]=4)[N:3]=3)[CH:30]=2)[CH2:33][CH2:32]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 178429393HCID 178429393, compound

Product 1

HCID 11396244HCID 11396244, compoundYield 37.6%

Reagents, catalysts & solvents 3

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 24813Phosphorus oxychlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-hydroxy-6-methyl-2-[2-{3-(pyrid-2-yl)isoxazol-5-yl}pyrrolidin-1-yl]pyrimidine (Method 30) (200 mg, 0.62 mmol) in phosphoryl chloride (7 ml) was heated at 70° C., under nitrogen for 30 minutes. The volatiles were removed by evaporation and the residue dissolved in DCM, washed with saturated sodium hydrogen carbonate solution, dried (MgSO4) and the solvent removed by evaporation. The crude product was then treated as described in Example 12, with 3-amino-5-cyclopropyl-1H-pyrazole (Method 7 of WO-03/048133) (120 mg, 0.98 mmol), and 4M hydrogen chloride solution in dioxane (0.65 ml) in NMP (5 ml) to give the title compound (100 mg, 37%).

Workup

  1. customThe volatiles were removed by evaporation
  2. dissolutionthe residue dissolved in DCM
  3. washwashed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. additionThe crude product was then treated

Sources & evidence

ORD record
ord-82a0bb3c9916437ab94cdeaf8ab1c44d
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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