Acetyl chloride → HCID 67546846, compound

HRID 1253682Notes

Reaction equation

HRID 1253682 reaction equation
C([Cl:4])(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)[CH2:12]2)=[CH:7][CH:6]=1>C(O)C>[ClH:4].[ClH:4].[ClH:4].[N:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:20][CH2:19][CH2:18][NH:17][CH2:16]3)[CH2:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 66701191HCID 66701191, compound

Product 1

HCID 67546846HCID 67546846, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The synthesis was carried out analogously to the synthesis of amine AMN-07. For this, in step (i) tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate was reacted with 4-chloropyridinium chloride (yield: 41%). The Boc protective group was then split off. In step (ii), ethanol (6 ml) and acetyl chloride (0.27 ml, 3.94 mmol) were added to tert-butyl 2-(pyridin-4-yl)-2,7-diazaspiro[4.5]decane-7-carboxylate (0.25 g, 0.788 mmol) and the mixture was stirred at room temperature for 12 h. When the reaction was complete, the solvent was removed in vacuo. Yield: 0.23 g (89%).

Workup

  1. customThe Boc protective group was then split off
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1f1ca354bd1142959cc6b130d589fbf0
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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