2-Phenylpyrrolidine → HCID 16037216, compound

HRID 1806260Notes

Reaction equation

HRID 1806260 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([CH:26]=O)[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[C:31]1([CH:37]2[CH2:41][CH2:40][CH2:39][NH:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O>[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([CH2:26][N:38]5[CH2:39][CH2:40][CH2:41][CH:37]5[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:4])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 2618922-PhenylpyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 577327033-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 16037216HCID 16037216, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (50 mg, 0.11 mmol) in DMSO (2.0 mL) was added 2-phenylpyrrolidine (147 mg, 1.0 mmol). The reaction mixture was then reacted in a microwave at 120° C. for 10 min. Sodium triacetoxyborohydride (220 mg, 1.0 mmol) was then added and the reaction was reacted at room temperature overnight. It was then purified by Gilson Preparatory HPLC to give 14.0 mg of the title compound (22%).

Workup

  1. customThe reaction mixture was then reacted in a microwave at 120° C. for 10 min
  2. customthe reaction was reacted at room temperature overnight
  3. customIt was then purified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-9ed808ac7cf548fcaad090d1d529ab5e
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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