Benzylamine → HCID 75080606, compound

HRID 1093155Notes

Reaction equation

HRID 1093155 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][C:20]([Cl:24])=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]12[O:32][CH:29]([CH2:30][CH2:31]1)[CH2:28][NH:27][CH2:26]2.C=CCCC=C.C(N)C1C=CC=CC=1.ClC(OC(Cl)C)=O>CCO.CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][C:20]([Cl:24])=[N:21][C:22]([N:27]4[CH2:26][CH:25]5[O:32][CH:29]([CH2:30][CH2:31]5)[CH2:28]4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 115981,5-HexadieneHCID 5213051-Chloroethyl chloroformateHCID 120692318-Oxa-3-azabicyclo[3.2.1]octaneHCID 44549632HCID 44549632, compound

Product 1

HCID 75080606HCID 75080606, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 1 mmol 1-(1-benzyl-piperidin-4-yl)-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine dissolved in EtOH (10 mL) was added 1 mmol 8-oxa-3-aza-bicyclo[3.2.1]octane, (Newth, F. H. and Wiggins, L. F. Journal of the Chemical Society. 1948, pages 155-158) prepared from 1,5-hexadiene by the four-step process of RuCl3-catalyzed NaIO4 oxidation, conversion to the bis tosylate, cyclization with benzyl amine, and deprotection with 1-chloroethyl chloroformate followed by methanol (Scheme 46). The reaction was stirred for 18 h. The solvents were evaporated and the reminder was triturated with diethyl ether/hexane. The solid was filtered off and washed with hexane. Drying on the fritted funnel provided a solid.

Workup

  1. customThe solvents were evaporated
  2. customthe reminder was triturated with diethyl ether/hexane
  3. filtrationThe solid was filtered off
  4. washwashed with hexane
  5. customDrying on the fritted funnel
  6. customprovided a solid

Sources & evidence

ORD record
ord-514ecf337bb54565843a903169077bcb
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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