1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid → HCID 178483557, compound

HRID 2243379Notes

Reaction equation

HRID 2243379 reaction equation
[CH:1]([C:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]([NH-:16])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=O.[NH:17]1[C:21]2[N:22]=[CH:23][CH:24]=[C:25]([C:26]([OH:28])=[O:27])[C:20]=2[CH:19]=[CH:18]1.[CH3:29][N:30]([CH3:44])[CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:36]=[C:37]([NH2:43])[C:38]([NH2:42])=[CH:39][C:40]=1[F:41]>CN(C)C=O>[NH:17]1[C:21]2[N:22]=[CH:23][CH:24]=[C:25]([C:26]([OH:28])=[O:27])[C:20]=2[CH:19]=[CH:18]1.[CH3:44][N:30]([CH3:29])[CH2:31][CH2:32][CH2:33][O:34][C:35]1[C:40]([F:41])=[CH:39][C:38]2[N:42]=[C:1]([C:3]3[C:15]4[C:14]5[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=5)[CH:8]([NH-:16])[C:7]=4[CH:6]=[CH:5][CH:4]=3)[NH:43][C:37]=2[CH:36]=1

Participants

5

Reactant 3

HCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acidHCID 578128554-(3-Dimethylaminopropoxy)-5-fluorobenzene-1,2-diamineHCID 131727972(4-Formyl-9h-fluoren-9(r,s)-yl)amide

Product 1

HCID 178483557HCID 178483557, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir, at room temperature under argon, a mixture of 100 mg of (4-formyl-9H-fluoren-9(R,S)-yl)amide of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid, prepared as in Example 234, 65 mg of 4-(3-dimethylaminopropoxy)-5-fluorobenzene-1,2-diamine, prepared in the previous stage, and 46 mg of ferric trichloride in 5 ml of anhydrous dimethylformamide. After 48 hours, evaporate the reaction medium to dryness and then purify the residue by flash chromatography on silica gel (20-40 μm), eluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (95/5 then 9/1 by volume). In this way, we obtain 42 mg of {4-[6-(3-dimethylaminopropoxy)-5-fluoro-1H-benzimidazol-2-yl]-9H-fluoren-9(R,S)-yl}amide 1H-pyrrolo[2,3-b]-pyridine-4-carboxylic acid, in the form of a yellow solid with the following characteristics:

Workup

  1. customevaporate the reaction medium to dryness
  2. custompurify the residue by flash chromatography on silica gel (20-40 μm)
  3. washeluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (95/5

Sources & evidence

ORD record
ord-fb6eb4b4cca04ac0ae217bdc0c220ade
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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