Ethyl 5-phenyl-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 1035197Notes

Reaction equation

HRID 1035197 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.[C:21]1([C:27]2[O:31][C:30]([C:32](OCC)=[O:33])=[N:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[F:20][C:8]1[CH:7]=[C:6]([O:5][CH:3]2[CH2:4][N:1]([C:32]([C:30]3[O:31][C:27]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[N:28][N:29]=3)=[O:33])[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 651752Ethyl 5-phenyl-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 41.2%

Procedure

Using a similar protocol as described in Example 10 employing 29D (0.10 g, 0.36 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.10 g, 0.46 mmol) as starting materials afforded 67 mg (41%) of 29 as a foam. 1H NMR (500 MHz, DMSO-d6): δ 2.10 (s, 3H), 2.12-2.50 (bm, 8H), 3.43 (s, 2H), 4.05-4.16 (m, 1H), 4.50-4.70 (m, 2H), 5.03-5.23 (m, 2H), 6.68-6.84 (m, 2H), 7.25-7.37 (m, 1H), 7.57-7.75 (m, 3H), 8.00-8.13 (m, 2H), MS (APCI+) m/z 452 [M+H]+, LC purity: 97%.

Sources & evidence

ORD record
ord-f8ec6fd884894167a9aea4288a35d2a7
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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