1,1,1-Trimethoxy-2-chloroethane → 5-(5-Chloromethyl-[1,3,4]oxadiazol-2-yl)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427512Notes

Reaction equation

HRID 2427512 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]([NH:26][NH2:27])=[O:25])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.CO[C:30](OC)(OC)[CH2:31][Cl:32]>>[Cl:32][CH2:31][C:30]1[O:25][C:24]([C:4]2[CH:5]=[C:6]3[C:10](=[C:2]([CH3:1])[CH:3]=2)[C:9](=[O:11])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:15][CH:14]=2)[CH2:7]3)=[N:26][N:27]=1

Participants

3

Reactant 2

HCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 579496127-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid hydrazide

Product 1

HCID 579496465-(5-Chloromethyl-[1,3,4]oxadiazol-2-yl)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

Procedure

7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid hydrazide (200.0 mg, 0.527 mmol) was stirred with trimethoxy chloroethane (2.0 mL) at 120° C. for two hours. The reaction was concentrated and column chromatography (50% EtOAc/Hexanes) provided the title compound as a yellow solid (28.0 mg). 1H NMR (300 MHz, CDCl3): δ 7.94 (s, 2H), 7.38 (d, 2H), 7.21 (d, 2H), 4.81 (s, 4H), 4.34 (s, 2H), 2.85 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-f221493c873f4d7681c75de1976f8649
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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