Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → (3-(4-((Dimethylamino)methyl)-2,3-difluorophenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1035205Notes

Reaction equation

HRID 1035205 reaction equation
Cl.Cl.[NH:3]1[CH2:6][CH:5]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]([CH3:17])[CH3:16])=[C:10]([F:18])[C:9]=2[F:19])[CH2:4]1.[C:20]1([C:26]2[O:30][C:29]([C:31](OCC)=[O:32])=[N:28][N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:16][N:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH:5]2[CH2:6][N:3]([C:31]([C:29]3[O:30][C:26]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[N:27][N:28]=3)=[O:32])[CH2:4]2)=[C:9]([F:19])[C:10]=1[F:18])[CH3:17]

Participants

3

Reactant 2

HCID 651752Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylateHCID 670164521-(4-(azetidin-3-yloxy)-2,3-difluorophenyl)-N,N-dimethylmethanamine dihydrochloride

Product 1

HCID 56598262(3-(4-((Dimethylamino)methyl)-2,3-difluorophenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneYield 15.7%

Procedure

Using a similar protocol as described in Example 36 employing 39A (0.32 g, 1.00 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.24 g, 1.10 mmol) as starting materials afforded 65 mg (15%) of 39 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.27 (s, 6H), 3.46 (s, 2H), 4.39 (dd, 1H), 4.65 (dd, 1H), 4.82 (m, 1H), 5.13 (m, 2H), 6.52 (t, 1H), 7.04 (t, 1H), 7.54 (t, 2H), 7.60 (t, 1H), 8.16 (d, 2H), MS (APCI+) m/z 415 [M+H]+, LC purity: 89%.

Sources & evidence

ORD record
ord-f5e600eda33b4a70a4394298643fcc74
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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