Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate → 1-[2-Fluoro-4-({1-[(5-phenyl-1,3,4-oxadiazol-2-yl)carbonyl]azetidin-3-yl}oxy)benzyl]-4-methylpiperazine

HRID 1035198Notes

Reaction equation

HRID 1035198 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:19]=[CH:18][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[C:8]([F:20])[CH:7]=2)[CH2:2]1.CO[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:33][C:32]([C:34](OCC)=[O:35])=[N:31][N:30]=2)=[CH:25][CH:24]=1>>[F:20][C:8]1[CH:7]=[C:6]([O:5][CH:3]2[CH2:4][N:1]([C:34]([C:32]3[O:33][C:29]([C:26]4[CH:25]=[CH:24][CH:23]=[CH:28][CH:27]=4)=[N:30][N:31]=3)=[O:35])[CH2:2]2)[CH:19]=[CH:18][C:9]=1[CH2:10][N:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 13407471Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylateHCID 666534801-(4-(Azetidin-3-yloxy)-2-fluorobenzyl)-4-methylpiperazine

Product 1

HCID 565979901-[2-Fluoro-4-({1-[(5-phenyl-1,3,4-oxadiazol-2-yl)carbonyl]azetidin-3-yl}oxy)benzyl]-4-methylpiperazineYield 32%

Procedure

Using a similar protocol as described in Example 10 employing 29D (0.10 g, 0.36 mmol) and ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate (0.11 g, 0.43 mmol) as starting materials afforded 52 mg (30%) of 29 as a foam.

Sources & evidence

ORD record
ord-217b1a61144a42bb88d174d46f96e085
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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