Methyl chloroformate → HCID 75080609, compound

HRID 1093169Notes

Reaction equation

HRID 1093169 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.C(=O)([O-])[O-].[K+].[K+].Cl[C:39]([O:41][CH3:42])=[O:40]>ClCCCl>[CH:25]12[O:30][CH:28]([CH2:27][CH2:26]1)[CH2:29][N:23]([C:22]1[N:21]=[C:20]([Cl:31])[N:19]=[C:18]3[N:14]([CH:11]4[CH2:12][CH2:13][N:8]([C:39]([O:41][CH3:42])=[O:40])[CH2:9][CH2:10]4)[N:15]=[CH:16][C:17]=13)[CH2:24]2

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 75080606HCID 75080606, compound

Product 1

HCID 75080609HCID 75080609, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
57.5 °C

Procedure

A suspension of 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 (1.0 g, 2.3 mmol) and potassium carbonate (0.94 g, 6.8 mmol) in 1,2-dichloroethane (15 mL) was treated with methyl chloroformate (0.53 mL, 6.8 mmol) and then heated for two hours in a 55-60° C. oil bath. The mixture was filtered through a pad of diatomaceous earth, eluting with dichloromethane. The filtrate was concentrated to dryness under reduced pressure to furnish methyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate. MS (ES+): 407.5, 409.6 (M+H)+

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washeluting with dichloromethane
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-986c284cc0724677853243c5c3ede36b
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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