Hydrochloric Acid → HCID 58314012, compound

HRID 624806Notes

Reaction equation

HRID 624806 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([Cl:23])[CH:17]=1.Cl>CCO>[Cl:23][C:18]1[CH:17]=[C:16]([NH:15][C:2]2[CH:7]=[C:6]([NH:8][CH:9]3[CH2:11][CH2:10]3)[N:5]3[N:12]=[CH:13][CH:14]=[C:4]3[N:3]=2)[CH:21]=[CH:20][C:19]=1[OH:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 775784-Amino-2-chlorophenolHCID 581966065-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 58314012HCID 58314012, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine (500 mg, 2.396 mmol) in EtOH (10 mL) was added 4-amino-2-chlorophenol (516 mg, 3.59 mmol) followed by concentrated HCl (0.218 mL, 2.64 mmol). The reaction mixture was stirred at reflux temperature for 4 days. Removed 5 mL of EtOH on rotavap followed by addition of 5 mL of diethyl ether. The resulting solid was filtered off and rinsed with diethyl ether. Dried under nitrogen to provide 582 mg (77%) of 2-chloro-4-(7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)phenol as the HCl salt. LCMS (ES): >95% pure, m/z 316 [M+1]+.

Workup

  1. temperatureat reflux temperature for 4 days
  2. customRemoved 5 mL of EtOH on rotavap
  3. additionfollowed by addition of 5 mL of diethyl ether
  4. filtrationThe resulting solid was filtered off
  5. washrinsed with diethyl ether
  6. customDried under nitrogen

Sources & evidence

ORD record
ord-5bc633dab9bb42edbb6d579ab0a0749d
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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