Potassium Carbonate → HCID 86629385, compound

HRID 1093157Notes

Reaction equation

HRID 1093157 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][C:20]([Cl:31])=[N:21][C:22]([N:23]4[CH2:29][CH:28]5[O:30][CH:25]([CH2:26][CH2:27]5)[CH2:24]4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.C([O-])([O-])=O.[K+].[K+]>ClCCCl>[Cl:31][C:20]1[N:19]=[C:18]2[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[N:15]=[CH:16][C:17]2=[C:22]([N:23]2[CH2:24][CH:25]3[O:30][CH:28]([CH2:27][CH2:26]3)[CH2:29]2)[N:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 75080606HCID 75080606, compound

Product 1

HCID 86629385HCID 86629385, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 1-(1-benzyl-piperidin-4-yl)-6-chloro-4-(8-oxa-3-aza-bicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (0.24 mmol) in 1,2-dichloroethane (2 mL) is added 1.9 mmol alpha-chloroethyl chloroformate (ACE-Cl) along with a small amount of K2CO3. The mixture is stirred for 5.5 h at RT. The reaction is quenched by addition of MeOH and the mixture is filtered and concentrated to dryness. The mixture is dissolved in MeOH and briefly heated to reflux. The title compound is obtained in quantitative yield by evaporation of MeOH. This material is used without further purification in the next step (reductive amination or acylation following the procedures disclosed previously, Scheme 30).

Workup

  1. customThe reaction is quenched by addition of MeOH
  2. filtrationthe mixture is filtered
  3. concentrationconcentrated to dryness
  4. dissolutionThe mixture is dissolved in MeOH
  5. temperaturebriefly heated to reflux

Sources & evidence

ORD record
ord-a91c02fe0d0d4ebf97ed0c2aedefe6cb
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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