Hydrochloric Acid → [1-(3,5-bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1H-[1,2,3]triazol-4-yl]-morpholin-4-yl-methanone

HRID 2251976Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Dissolve 1-(3,5-bis-trifluoromethyl-benzyl)-5-chloro-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester in morpholine (20 eq). Stir at 70° C. overnight then increase temp to 80° C. and continue stirring for another 60 hours. Cool to RT, pour into separatory funnel with EtOAc and 1N HCl. Separate layers and wash organic layer with 1N HCl and then with brine. Dry over MgSO4, filter, and concentrate. Purify via silica gel chromatography using a gradient of 1:1 to 1:5 hexanes:EtOAc to give the desired product. MS (IS) 494.2 (M+1). Rf=0.16 (1:1 Hexanes:EtOAc)

Workup

temperaturethen increase temp to 80° C.
stirringcontinue stirring for another 60 hours
temperatureCool to RT
washSeparate layers and wash organic layer with 1N HCl
dry with materialDry over MgSO4
filtrationfilter
concentrationconcentrate
customPurify via silica gel chromatography

Sources & evidence

ORD record: ord-99716637f51c4036a900e087b84d1919
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320994B2

Reaction notes

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