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

HRID 2182363Notes

Reaction equation

HRID 2182363 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. (b) 2-(1H-Indazol-3-yl)-1H-benzoimidazole-5-sulfonic acid benzylamide

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-0ef54b92252d4ce0a7783ed5201c9223
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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