Trimethyl orthoformate → 3-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide

HRID 20556Notes

Reaction equation

HRID 20556 reaction equation
[OH:1][NH:2][C:3](=[NH:32])[C:4]1[CH:31]=[CH:30][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C@@H:25]([CH3:29])[CH2:26][O:27][CH3:28])[CH:23]=2)[C:12]([NH:14][C:15]2[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=2)=[O:13])=[CH:6][CH:5]=1.[CH:33](OC)(OC)OC>>[CH3:28][O:27][CH2:26][C@H:25]([CH3:29])[O:24][C:22]1[CH:21]=[C:11]([CH:10]=[C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([C:3]3[N:32]=[CH:33][O:1][N:2]=3)=[CH:31][CH:30]=2)[CH:23]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=1)=[O:13]

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 178495721HCID 178495721, compound

Product 1

HCID 115180333-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide

Conditions

Temperature
55 °C

Procedure

3-{4-[(Hydroxyamino)(imino)methyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide was taken up in trimethyl orthoformate (3 mL) and 2 drops of borontrifluoroetherate added. The resulting solution was heated to 55° C. in a CEM explorer microwave for 80 mins. The volatiles were removed under reduced pressure and the resulting oil chromatographed on silica, eluting with 0-100% ethyl acetate in iso-hexane, to give the desired compound as a white foam (295 mg)

Workup

  1. addition2 drops of borontrifluoroetherate added
  2. customThe volatiles were removed under reduced pressure
  3. customthe resulting oil chromatographed on silica
  4. washeluting with 0-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-2597c2f8d12542899d7e61dc3fdf9d90
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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