Acetyl chloride → HCID 67546430, compound

HRID 1253681Notes

Reaction equation

HRID 1253681 reaction equation
C([Cl:4])(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:27][CH2:26][CH2:25][C:13]3([CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]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[CH2:27][CH2:26][CH2:25][C:13]3([CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 66700746HCID 66700746, compound

Product 1

HCID 67546430HCID 67546430, 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-2-carboxylate was reacted with 4-chloropyridinium chloride (yield: 53%). The Boc protective group was then split off. In step (ii), ethanol (8 ml) and acetyl chloride (0.37 ml, 5.355 mmol) were added to tert-butyl 7-(pyridin-4-yl)-2,7-diazaspiro[4.5]decane-2-carboxylate (0.34 g, 1.071 mmol) and the mixture was stirred at room temperature for 12 h. When the reaction was complete, the solvent was removed in vacuo. Yield: 0.28 g (80%)

Workup

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

Sources & evidence

ORD record
ord-0c603b5728f5436bac692a7239adc74a
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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