1,2-Dichloroethane → HCID 71542822, compound

HRID 1776619Notes

Reaction equation

[C:1]([C:4]([O:6][C@H:7]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([O:28][CH2:29][CH:30]2[CH2:32][CH2:31]2)[CH:19]=1)[CH2:8][C:9]1[C:14]([Cl:15])=[CH:13][N+:12]([O-:16])=[CH:11][C:10]=1[Cl:17])=[O:5])([OH:3])=O.C(Cl)CCl.[CH3:37][O:38][C:39]1[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=[CH:42][C:40]=1[NH2:41]>CN(C=O)C.Cl>[Cl:17][C:10]1[CH:11]=[N+:12]([O-:16])[CH:13]=[C:14]([Cl:15])[C:9]=1[CH2:8][C@@H:7]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:26])[F:27])=[C:20]([O:28][CH2:29][CH:30]2[CH2:31][CH2:32]2)[CH:19]=1)[O:6][C:4](=[O:5])[C:1]([NH:41][C:40]1[CH:42]=[CH:43][C:44]([N+:46]([O-:48])=[O:47])=[CH:45][C:39]=1[O:38][CH3:37])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-4-(2-(carboxycarbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (50 mg, 0.10 mmol) was dissolved in DMF (5 ml), then EDC (29.2 mg, 0.15 mmol) was added. 2-methoxy-4-nitroaniline (34.2 mg, 0.2 mmol) was added at 0° C., and the mixture was stirred at 0° C. for 2 hours. The reaction was diluted with HCl 1M and extracted with EtOAc. The organic phase was dried over Na2SO4 and evaporated under vacuum. The crude product was purified by Preparative reverse-phase HPLC to give 21 mg of the title product. (Yield: 32%).

Workup

extractionextracted with EtOAc
dry with materialThe organic phase was dried over Na2SO4
customevaporated under vacuum
customThe crude product was purified by Preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-370b899633fe4ff9b108904f558d06ed
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265768B2

Reaction notes

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