4-Amino-1-methylpiperidine → HCID 68470735, compound

HRID 506813Notes

Reaction equation

HRID 506813 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:16]4[N:17]=[CH:18][CH:19]=[C:20]([CH:21]=O)[C:15]=4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:34][CH3:35].[NH2:36][CH:37]1[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]1>>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:25])=[O:26])[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH:36][CH:37]5[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]5)=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:34][CH3:35]

Participants

3

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 866186352-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde

Product 1

HCID 68470735HCID 68470735, compoundYield 77.8%

Procedure

The product is prepared by following the procedure described in example 34 stage (j), starting with 0.3 g of 2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde and 0.348 g of 4-amino-1-methylpiperidine instead of the cyclopropylamine used in example 34 stage (j). After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluents), 0.28 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]-(1-methylpiperidin-4-yl)amine is obtained with the following characteristics:

Workup

  1. customThe product is prepared
  2. customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluents)

Sources & evidence

ORD record
ord-f78536cd82554a88a704af962c960e68
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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