Triethyl phosphite → N-cyclopropyl-5-(diethylphosphonomethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

HRID 1717370Notes

Reaction equation

Br[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)[N:6]=[N:5][C:4]=1[C:19]([NH:21][CH:22]1[CH2:24][CH2:23]1)=[O:20].[P:25]([O:32]CC)([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]>>[CH:22]1([NH:21][C:19]([C:4]2[N:5]=[N:6][N:7]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=3)[C:3]=2[CH2:2][P:25]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:32])=[O:20])[CH2:24][CH2:23]1

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 685163445-(bromomethyl)-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 86629812N-cyclopropyl-5-(diethylphosphonomethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

Conditions

Temperature: 120 °C

Procedure

5-(Bromomethyl)-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (890 mg) obtained in Example 321a) was dissolved in triethyl phosphite (2 ml), and the mixture was stirred at 120° C. for 3 days. An excess amount of triethyl phosphite was evaporated under reduced pressure, and the obtained residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=4/1) to give the title compound as a colorless oil (640 mg).

Workup

customAn excess amount of triethyl phosphite was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record: ord-e9154755c03f4fc48e2817a3f542ab5c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803822B2

Reaction notes

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