3-Oxetanone → 6-Chloro-1-[6-[4-(oxetan-3-yl)-1,4-diazepan-1-yl]-2-pyridyl]pyrazolo[4,3-c]pyridine

HRID 57953

Reaction equation

HRID 57953 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N:17]4[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[N:12]=3)[C:4]=2[CH:3]=1.[O:24]1[CH2:27][C:26](=O)[CH2:25]1>ClCCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N:17]4[CH2:23][CH2:22][CH2:21][N:20]([CH:26]5[CH2:27][O:24][CH2:25]5)[CH2:19][CH2:18]4)[N:12]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 150242543-OxetanoneHCID 867070506-Chloro-1-[6-(1,4-diazepan-1-yl)-2-pyridyl]pyrazolo[4,3-c]pyridine

Product 1

HCID 867071386-Chloro-1-[6-[4-(oxetan-3-yl)-1,4-diazepan-1-yl]-2-pyridyl]pyrazolo[4,3-c]pyridineYield 63%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-chloro-1-[6-(1,4-diazepan-1-yl)-2-pyridyl]pyrazolo[4,3-c]pyridine (0.4094 mmol; 134.6 mg), oxetan-3-one (0.4912 mmol; 35.40 mg), and Molecular sieve (4A) in 1,2-dichloroethane (12 ml) was stirred at room temperature for 4 hours. STAB (0.6141 mmol; 137.0 mg) was added. The reaction was stirred for 3 days. The mixture was filtered through Celite. The filtrate was concentrated and the residue was purified on silica eluted with 0 to 5% MeOH in DCM to afford 6-chloro-1-[6-[4-(oxetan-3-yl)-1,4-diazepan-1-yl]-2-pyridyl]pyrazolo[4,3-c]pyridine (99.2 mg, 63%).

Workup

  1. additionSTAB (0.6141 mmol; 137.0 mg) was added
  2. stirringThe reaction was stirred for 3 days
  3. filtrationThe mixture was filtered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified on silica
  6. washeluted with 0 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-6e997d4893474b41b11d9ff12a2b1149
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Linked notes

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