Ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate → 2-(4-Chlorophenyl)-5-({3-[2-methyl-4-(pyrrolidin-1-ylmethyl)phenoxy]azetidin-1-yl}carbonyl)-1,3,4-oxadiazole

HRID 1035183Notes

Reaction equation

HRID 1035183 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:17]=[CH:16][C:9]([CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:8][C:7]=2[CH3:18])[CH2:2]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][C:29]([C:31](OCC)=[O:32])=[N:28][N:27]=2)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[O:30][C:29]([C:31]([N:1]3[CH2:2][CH:3]([O:5][C:6]4[CH:17]=[CH:16][C:9]([CH2:10][N:11]5[CH2:12][CH2:13][CH2:14][CH2:15]5)=[CH:8][C:7]=4[CH3:18])[CH2:4]3)=[O:32])=[N:28][N:27]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 46742983Ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylateHCID 666561701-(4-(Azetidin-3-yloxy)-3-methylbenzyl)pyrrolidine

Product 1

HCID 565978502-(4-Chlorophenyl)-5-({3-[2-methyl-4-(pyrrolidin-1-ylmethyl)phenoxy]azetidin-1-yl}carbonyl)-1,3,4-oxadiazoleYield 58%

Procedure

Using a similar protocol as described in Example 16 employing 19B (0.20 g, 0.80 mmol) and ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate (0.22 g, 0.88 mmol) as starting materials afforded 0.21 g (46%) of 19 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.72-1.84 (m, 4H), 2.35 (s, 3H), 2.43-2.58 (m, 4H), 3.54 (s, 2H), 4.28-4.36 (m, 1H), 4.59-4.68 (m, 1H), 4.70-4.78 (m, 1H), 5.02-5.16 (m, 2H), 6.55 (d, 1H), 6.60 (s, 1H), 7.23 (d, 1H), 7.52 (d, 2H), 8.11 (d, 2H), MS (APCI+) m/z 453 [M+H]+, LC purity: 94%.

Sources & evidence

ORD record
ord-1ba986e6abb24ee0875fe51d652d7e64
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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