Oxalyl chloride → 4-[3-(5-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-N,N-bis(2-methoxyethyl)-2-nitroaniline

HRID 1950862Notes

Reaction equation

HRID 1950862 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][CH2:9][CH2:10][N:11]([CH2:24][CH2:25][O:26][CH3:27])[C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22].[F:28][C:29]1[CH:30]=[CH:31][C:32]([O:39][CH3:40])=[C:33]([C:35](=[N:37]O)[NH2:36])[CH:34]=1.CCN(C(C)C)C(C)C>>[F:28][C:29]1[CH:30]=[CH:31][C:32]([O:39][CH3:40])=[C:33]([C:35]2[N:36]=[C:16]([C:15]3[CH:19]=[CH:20][C:12]([N:11]([CH2:10][CH2:9][O:8][CH3:7])[CH2:24][CH2:25][O:26][CH3:27])=[C:13]([N+:21]([O-:23])=[O:22])[CH:14]=3)[O:18][N:37]=2)[CH:34]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 596065384-[Bis(2-methoxyethyl)amino]-3-nitrobenzoic acidHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 252566544-[3-(5-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-N,N-bis(2-methoxyethyl)-2-nitroaniline

Procedure

Oxalyl chloride (190 mg; 1.5 mmol; 3 eq.), Intermediate 31 (149 mg; 0.5 mmol; 1 eq.), Intermediate 23 (92 mg; 0.5 mmol, 1 eq.) and DIEA (194 mg; 1.5 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography (c-hexane/ethyl acetate, 50/50) followed by crystallisation from Et2O/n-pentane afforded the title compound as a yellow solid.

Workup

  1. customPurification by column chromatography (c-hexane/ethyl acetate, 50/50)
  2. customfollowed by crystallisation from Et2O/n-pentane

Sources & evidence

ORD record
ord-fc91a1ac56d84611af168398ce03c7c1
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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