Diphenyl chlorophosphate → Diphenyl N-[4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]phenylsulfonyl]phosphoramidate

HRID 1987188Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=1.[P:26](Cl)([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([NH:25][P:26](=[O:27])([O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)(=[O:23])=[O:24])=[CH:20][CH:21]=2)[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=1

Participants

Reactant 2

HCID 75654Diphenyl chlorophosphate

HCID 213053Cimicoxib

Product 1

HCID 10008930Diphenyl N-[4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]phenylsulfonyl]phosphoramidateYield 10%

Procedure

Following a similar procedure to that described in sections a and b of example 12, but using 4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide (obtained as described in WO 00/23426) instead of 4-[4-chloro-5-(4-ethoxyphenyl)imidazol-1-yl]benzenesulfonamide and diphenyl chlorophosphate instead of diethyl chlorophosphate, the title compound of the example was obtained in 10% yield.

Sources & evidence

ORD record: ord-da50e247c9cb43d7adbe96adcf3257b4
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550497B2

Reaction notes

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