Nitromethane → 1-(6-(6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-3-(nitromethyl)azetidin-3-ol

HRID 57992Notes

Reaction equation

HRID 57992 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[CH:11][C:10]3[CH:13]=[N:14][N:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:25][C:24](=[O:26])[CH2:23]5)[CH:19]=[CH:18][CH:17]=4)[C:9]=3[CH:8]=2)[CH:4]=[N:3]1.[N+:27]([CH3:30])([O-:29])=[O:28].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[CH:11][C:10]3[CH:13]=[N:14][N:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:25][C:24]([CH2:30][N+:27]([O-:29])=[O:28])([OH:26])[CH2:23]5)[CH:19]=[CH:18][CH:17]=4)[C:9]=3[CH:8]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 867071781-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)azetidin-3-one

Product 1

HCID 867071771-(6-(6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-3-(nitromethyl)azetidin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)azetidin-3-one (1.1 g) in DCM (10 mL) at 20° C. was added nitromethane (1 mL) and triethylamine (0.5 mL). The mixture was stirred at ambient temperature for 2 hours. It was concentrated under reduced pressure to afford a white solid. The crude product (1.3 g), 1-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-3-(nitromethyl)azetidin-3-ol, was used for next step without further purification. MS (ESI) m/z: 407 [M+H]+.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. customto afford a white solid
  3. customThe crude product (1.3 g), 1-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-3-(nitromethyl)azetidin-3-ol, was used for next step without further purification

Sources & evidence

ORD record
ord-1f30870a19f8451dbe5a72c3c5594434
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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