Sodium Carbonate → 5-(cyclopropylmethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid

HRID 1717291Notes

Reaction equation

[CH:1]1([CH2:4][C:5](=O)[CH2:6][C:7]([O:9]CC)=[O:8])[CH2:3][CH2:2]1.[N:13]([C:16]1[CH:26]=[CH:25][C:19]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)=[N+:14]=[N-:15].[O-]CC.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH:1]1([CH2:4][C:5]2[N:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=3)[N:14]=[N:15][C:6]=2[C:7]([OH:9])=[O:8])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 4-cyclopropyl-3-oxobutyrate (1.20 g, 7.05 mmol, 1.2 eq.) obtained in Example 96a) and 4-azido-N-ethylbenzamide (1.20 g, 5.88 mmol) were dissolved in ethanol (25 ml), sodium ethoxide (556 mg, 7.35 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 80° C. for 2.5 hr. 2% Aqueous sodium carbonate solution (40 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with water (20 ml) and washed twice with ethyl acetate-hexane (2:1, 50 ml). The organic layer was extracted with 1% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, acidified (pH<3) with 6N hydrochloric acid, and stood still at 5° C. The precipitate was collected by filtration, washed with cold water and dried to give the title compound as a pale-brown powder (1.88 g, 5.98 mmol, 101.7%).

Workup

customwas evaporated
additionthe residue was diluted with water (20 ml)
washwashed twice with ethyl acetate-hexane (2:1, 50 ml)
extractionThe organic layer was extracted with 1% aqueous sodium carbonate solution (20 ml)
customstood still at 5° C
filtrationThe precipitate was collected by filtration
washwashed with cold water
customdried

Sources & evidence

ORD record: ord-48dcebec2fa6453fa2e17c2eff64d7a1
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803822B2

Reaction notes

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