4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178526767, compound

HRID 2274396Notes

Reaction equation

HRID 2274396 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:19])[C:5]([NH2:18])=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[N+:20]([C:23]1[C:24]([CH:34]=O)=[N:25][N:26]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:27]=1)([O-:22])=[O:21]>CO>[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][C:5]2[NH:18][C:34]([C:24]3[C:23]([N+:20]([O-:22])=[O:21])=[CH:27][N:26]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[N:25]=3)=[N:19][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 224778374-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehydeHCID 688406714-Fluoro-5-(3-piperidin-1-ylpropoxy)benzene-1,2-diamine

Product 1

HCID 178526767HCID 178526767, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 200 mg of 4-fluoro-5-(3-piperidin-1-ylpropoxy)benzene-1,2-diamine and 181 mg of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde in 15 mL of methanol is stirred at ambient temperature over night. The reaction medium is concentrated to dryness under vacuum in a rotary evaporator. The reaction crude is purified by flash chromatography on a 20 g silica cartridge, eluent: 100/0 to 80/20 dichloromethane/methanol. 280 mg of 5-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-(3-piperidin-1-ylpropoxy)-1H-benzimidazoleare isolated in the form of a red lake. Analytical LC/MS: Tr=2.51 min, [M+H]+=472.97 DAD=36%.

Workup

  1. concentrationThe reaction medium is concentrated to dryness under vacuum in a rotary evaporator
  2. customThe reaction crude
  3. customis purified by flash chromatography on a 20 g silica cartridge, eluent
  4. custom280 mg of 5-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-(3-piperidin-1-ylpropoxy)-1H-benzimidazoleare isolated in the form of a red lake
  5. customTr=2.51 min, [M+H]+=472.97 DAD=36%

Sources & evidence

ORD record
ord-c862ea315f8e43a6baa7f9e9e76c6c1a
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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