Cyclopentanecarbaldehyde → N-(cyclopentylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-4-(methylsulfonyl)aniline

HRID 633561Notes

Reaction equation

HRID 633561 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:11]([C:12]3[CH:18]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:16]=[CH:15][C:13]=3[NH2:14])=[CH:10][N:9]([CH3:23])[C:8]=12.[CH:24]1([CH:29]=O)[CH2:28][CH2:27][CH2:26][CH2:25]1>ClC(Cl)C.C(O)(=O)C>[CH:24]1([CH2:29][NH:14][C:13]2[CH:15]=[CH:16][C:17]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:18][C:12]=2[C:11]2[C:7]3[C:8](=[C:3]([O:2][CH3:1])[N:4]=[CH:5][CH:6]=3)[N:9]([CH3:23])[CH:10]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 70106CyclopentanecarbaldehydeHCID 903876822-(7-Methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-4-(methylsulfonyl)benzenamine

Product 1

HCID 90417402N-(cyclopentylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-4-(methylsulfonyl)anilineYield 31%

Reagents, catalysts & solvents 1

HCID 18768099Dichloroethane acetic acidSolvent

Procedure

The product from Example 44A (55 mg, 0.166 mmol) and cyclopentanecarbaldehyde (58.64 mg, 0.597 mmol) in dichloroethane/acetic acid (1:1, 1 mL) was heated in a sealed tube at 60° C. for 24 hours, cooled, and concentrated. Purification by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%) afforded the title compound (0.021 g, 31%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customPurification by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%)

Sources & evidence

ORD record
ord-3a2bfdcd3b7144f98e50d2836b0636cb
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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