Acetyl chloride → HCID 66701188, compound

HRID 1253680Notes

Reaction equation

HRID 1253680 reaction equation
C([Cl:4])(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:28][CH2:27][CH2:26][C:13]3([CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][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[CH2:28][CH2:27][CH2:26][C:13]3([CH2:14][CH2:15][CH2:16][NH:17][CH2:18]3)[CH2:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 66701123HCID 66701123, compound

Product 1

HCID 66701188HCID 66701188, 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 2,8-diazaspiro[5.5]undecane-2-carboxylate was reacted with 4-chloropyridinium chloride (yield: 66%). The Boc protective group was then split off. In step (ii), ethanol (8 ml) and acetyl chloride (0.45 ml, 6.335 mmol) were added to tert-butyl 8-(pyridin-4-yl)-2,8-diazaspiro[5.5]undecane-2-carboxylate (0.42 g, 1.267 mmol) and the mixture was stirred at room temperature for 12 h. When the reaction was complete, the solvent was removed in vacuo. Yield: 0.39 g (90%)

Workup

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

Sources & evidence

ORD record
ord-5516dabc27524bc2b8e410c4c2de3b0b
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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