Triethylamine → N-Benzyloxy-4-chloro-2-cyclopropylamino-5-fluoro-benzamide

HRID 2270234Notes

Reaction equation

HRID 2270234 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([NH:12][CH:13]2[CH2:15][CH2:14]2)[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH2:29]([O:36][NH2:37])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>C1COCC1>[CH2:29]([O:36][NH:37][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([F:11])[C:2]([Cl:1])=[CH:3][C:4]=1[NH:12][CH:13]1[CH2:15][CH2:14]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 102312Benzyloxyamine hydrochlorideHCID 226328834-Chloro-2-cyclopropylamino-5-fluoro-benzoic acid

Product 1

HCID 22632989N-Benzyloxy-4-chloro-2-cyclopropylamino-5-fluoro-benzamideYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure of Example A, 4-chloro-2-cyclopropylamino-5-fluoro-benzoic acid (Example C-3, 2.0 g, 8.7 mmol) was reacted with carbonyldiimidazole (1.7 g, 10.5 mmol), O-benzylhydroxylamine hydrochloride (1.67 g, 10.5 mmol), and triethylamine (1.5 mL, 10.5 mmol) in THF (50 mL) to give 2.92 g of the title compound.

Sources & evidence

ORD record
ord-a1474153b06c40c3958968405065b507
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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