4-Propyl-1,2-benzenediamine → HCID 178438820, compound

HRID 2064605Notes

Reaction equation

HRID 2064605 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([NH2:11])[C:7]([NH2:10])=[CH:8][CH:9]=1)[CH2:2][CH3:3].S(=O)(O)[O-].[Na+].[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH:26]=O)=[N:18]1>CN(C)C=O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]2[NH:10][C:26]([C:19]3[C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:17][N:18]=3)=[N:11][C:6]=2[CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 137634154-Propyl-1,2-benzenediamineHCID 23665763Sodium BisulfiteHCID 178520025HCID 178520025, compound

Product 1

HCID 178438820HCID 178438820, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

A stirred solution of 4-propyl-benzene-1,2-diamine [57 mg, Reference Example 30(d)] and sodium bisulfite (40 mg) in dimethylformamide (2 ml) was treated with indazole-3-carboxaldehyde [Reference Example 6(l)]. The reaction mixture was heated in a Smith Creator microwave at 200° C. for 13 minutes then partitioned between ethyl acetate and water. The organic layer was washed with brine, then dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (3:1) to give 3-(5-n-propyl-1H-benzoimidazol-2-yl)-1H-indazole (74 mg) as a pale brown solid. MS: 277.3 (M+H)+. HPLC (METHOD B1): RT=12.81 minutes.

Workup

  1. customthen partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (3:1)

Sources & evidence

ORD record
ord-eb32e79a783b44b4af49464201d03b10
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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