Benzoyl chloride → HCID 17751431, compound

HRID 643895Notes

Reaction equation

HRID 643895 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:16][C:15](=[O:17])[NH:14][S:13]1(=[O:19])=[O:18])[CH:8]=[C:7]([CH2:20][CH2:21][CH:22]([CH3:25])[C:23]#[N:24])[CH:6]=[CH:5]2.CC(C)([O-])C.[K+].[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[C:23]([CH:22]([CH3:25])[CH2:21][CH2:20][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([O:1][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:11]([N:12]1[CH2:16][C:15](=[O:17])[NH:14][S:13]1(=[O:19])=[O:18])=[CH:10]2)#[N:24]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 23665647Potassium tert-butoxideHCID 66750741HCID 66750741, compound

Product 1

HCID 17751431HCID 17751431, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[6-hydroxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-2-methylbutyronitrile (Example 9-3, 29 mg, 0.08 mmol) in DMF (0.6 mL) is added potassium t-butoxide (0.097 mL, 0.097 mmol) followed by benzoyl chloride. The reaction is stirred at RT until the reaction is completed. The reaction mixture is then purified by HPLC to give the title compound: Retention time 1.23 min (Method A); (M+H)+=462.

Workup

  1. customThe reaction mixture is then purified by HPLC

Sources & evidence

ORD record
ord-7aa2209c5d274332900b4117a1106fee
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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