Acetyl chloride → 7-(3-Azaspiro[5.5]undecan-9-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine dihydrochloride

HRID 1253709Notes

Reaction equation

HRID 1253709 reaction equation
C([Cl:4])(=O)C.[N:5]1[CH:6]=[N:7][N:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:31][CH2:30][C:17]4([CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)[CH2:16][CH2:15]3)[CH2:10][C:9]=12>C(O)C>[ClH:4].[ClH:4].[CH2:18]1[C:17]2([CH2:30][CH2:31][CH:14]([N:11]3[CH2:12][CH2:13][N:8]4[N:7]=[CH:6][N:5]=[C:9]4[CH2:10]3)[CH2:15][CH2:16]2)[CH2:22][CH2:21][NH:20][CH2:19]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 66701117tert-Butyl 9-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-azaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 667007687-(3-Azaspiro[5.5]undecan-9-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine dihydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (5 eq.) was added to an ice-cold solution of tert-butyl 9-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-azaspiro[5.5]undecane-3-carboxylate (0.666 mmol, 1 eq.) in ethanol (5 ml). The reaction mixture was stirred at room temperature for overnight. The white solid was filtered out, washed with diethyl ether and dried in vacuo. Yield: 91%

Workup

  1. filtrationThe white solid was filtered out
  2. washwashed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-bda6fce53b6e4a20a8e7a6b0529e2cde
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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