Hydrochloric Acid → 8-(piperazin-1-yl)-5-(thiophen-2-yl)tetrazolo[1,5-a]pyrazine HCl salt

HRID 1045735Notes

Reaction equation

HRID 1045735 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]2[N:12]=[N:13][N:14]=[C:10]2[C:9]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[N:8][CH:7]=1.C1COCC1.[ClH:33]>CO.C(Cl)Cl>[ClH:33].[N:15]1([C:9]2[C:10]3[N:11]([N:12]=[N:13][N:14]=3)[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][N:8]=2)[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 58447033tert-Butyl 4-(5-(thiophen-2-yl)tetrazolo[1,5-a]pyrazin-8-yl)piperazine-1-carboxylate

Product 1

HCID 673934078-(piperazin-1-yl)-5-(thiophen-2-yl)tetrazolo[1,5-a]pyrazine HCl saltYield 79%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A 1 L round bottom flask was charged with tert-butyl 4-(5-(thiophen-2-yl)tetrazolo[1,5-a]pyrazin-8-yl)piperazine-1-carboxylate (210 g, 0.54 mol) and THF (400 mL). To this solution was added concentrated HCl (40 mL) dropwise in an ice-water bath. The resulting solution was stirred at reflux for 0.5 h. Reaction progress was monitored by TLC (MeOH/CH2Cl2=1:10). Work-up: the resulting crystalline solid was collected by filtration, washed with EtOH (200 mL), and dried to afford 139 g (79%) of the product as a yellow solid. MS m/z: 288 (M+H+).

Workup

  1. temperatureat reflux for 0.5 h
  2. customReaction progress
  3. filtrationthe resulting crystalline solid was collected by filtration
  4. washwashed with EtOH (200 mL)
  5. customdried

Sources & evidence

ORD record
ord-1f302c9d43f2480ca5cf8d960b29d26a
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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