Dichloromethane → HCID 68757503, compound

HRID 387565Notes

Reaction equation

HRID 387565 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:10]1[C:11]([N:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)=[C:12]2[CH:18]=[N:17][N:16](CC3C=CC(OC)=CC=3)[C:13]2=[N:14][CH:15]=1)#[N:9].C(Cl)[Cl:42]>>[ClH:42].[ClH:42].[N:28]1([C:11]2[C:10]([C:8]#[N:9])=[CH:15][N:14]=[C:13]3[NH:16][N:17]=[CH:18][C:12]=23)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acid2×HCID 68760394HCID 68760394, compound

Product 1

HCID 68757503HCID 68757503, compoundYield 70%

Procedure

TFA (1 mL) was added to tert-butyl 4-(5-cyano-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.158 g, 0.352 mmol) in DCM (5 mL) and stirred at room temperature for 1 hour. The reaction was then concentrated to dryness and dried under vacuum for 3 hours. TFA (1.1 mL, 14.7 mmol) was added, and the mixture was heated at 65° C. for 2 hours. The reaction was concentrated to dryness. The resulting residue was dissolved in DCM (3 mL), and HCl in ether (2 mL, 2M) and ether (5 mL) were added. The resulting solid was collected by filtration to give 4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile dihydrochloride (0.091 g, 70%). MS APCI (+) m/z 229.1 detected.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. customdried under vacuum for 3 hours
  3. temperaturethe mixture was heated at 65° C. for 2 hours
  4. concentrationThe reaction was concentrated to dryness
  5. dissolutionThe resulting residue was dissolved in DCM (3 mL)
  6. additionHCl in ether (2 mL, 2M) and ether (5 mL) were added
  7. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-0e8bf9d7052e4054806b94508e0a2c3d
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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