Sodium Iodide → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(1-{2-[(2-hydroxyethyl)(methyl)amino]ethyl}-1H-pyrazol-4-yl)-1H-indole-7-carboxamide

HRID 562242Notes

Reaction equation

HRID 562242 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]3[C:15](=[C:16]([C:18]([NH2:20])=[O:19])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[CH:6]=[N:5]1.[CH3:32][NH:33][CH2:34][CH2:35][OH:36].[I-].[Na+]>O1CCCC1>[CH2:30]([S:27]([N:24]1[CH2:25][CH2:26][CH:21]([C:12]2[C:11]3[C:15](=[C:16]([C:18]([NH2:20])=[O:19])[CH:17]=[C:9]([C:7]4[CH:6]=[N:5][N:4]([CH2:3][CH2:2][N:33]([CH2:34][CH2:35][OH:36])[CH3:32])[CH:8]=4)[CH:10]=3)[NH:14][CH:13]=2)[CH2:22][CH2:23]1)(=[O:29])=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 80162-(Methylamino)ethanolHCID 66722972HCID 66722972, compound

Product 1

HCID 577326443-[1-(ethylsulfonyl)-4-piperidinyl]-5-(1-{2-[(2-hydroxyethyl)(methyl)amino]ethyl}-1H-pyrazol-4-yl)-1H-indole-7-carboxamideYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-[1-(2-chloroethyl)-1H-pyrazol-4-yl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (30 mg, 0.065 mmol), 2-(methylamino)ethanol (500 μL, 6.5 mmol) and sodium iodide (3 mg, 0.016 mmol) in tetrahydrofuran (1 mL) was reacted in a microwave for 2 h at 130° C. An aqueous work-up was performed on the resulting mixture. This was then purified by Gilson Preparatory HPLC to give 9 mg of the title compound (17%).

Workup

  1. customThis was then purified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-de7c653d51ab421ba6b84b6f8c6d52bc
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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