Hydrochloric Acid → HCID 57544433, compound

HRID 418259Notes

Reaction equation

HRID 418259 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.C(OC([NH:18][NH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:22][CH2:21]1)=O)(C)(C)C.C(N(CC)CC)C.Cl>ClCCl.CCOCC.CCOC(C)=O.O>[Cl:10][C:6]1[N:5]=[CH:4][N:3]=[C:2]2[N:19]([CH:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH2:24][CH2:25]3)[N:18]=[CH:8][C:7]=12

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehydeHCID 11573844Benzyl 4-[2-(tert-butoxycarbonyl)hydrazinyl]piperidine-1-carboxylate

Product 1

HCID 57544433HCID 57544433, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,6-dichloropyrimidine-5-carbaldehyde (1.089 g, 6.15 mmol) and benzyl 4-(2-(tert-butoxycarbonyl)hydrazinyl)piperidine-1-carboxylate from Example 12A (2.15 g, 6.15 mmol) in dichloromethane (25 mL) was added triethylamine (2.144 mL, 15.38 mmol). The resulting solution was allowed to stir at ambient temperature for 3 h. The reaction flask was placed in a bath of cold water, then there was added 2N HCl in ether slowly and directly to the reaction mixture. Stirred 5 minutes and then diluted with EtOAc and washed with 1N HCl, sat'd aq sodium bicarbonate and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford Example 12B, benzyl 4-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate, as an oil (2.26 g) which was pure enough to be used without purification. LRMS (ESI): 372.2 (M+H)+.

Workup

  1. stirringStirred 5 minutes
  2. washwashed with 1N HCl
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-458f65493fa34c8694afcf7fa086a115
Source dataset
uspto-grants-2012_01
Patent number
US08093257B2

Reaction notes

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