4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenol → (3-(4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)methanone

HRID 1639503Notes

Reaction equation

HRID 1639503 reaction equation
[CH2:1]1[C:4]2([CH2:7][N:6]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=3)[CH2:5]2)[CH2:3][O:2]1.CS(O[CH:21]1[CH2:24][N:23]([C:25]([C:27]2[O:28][C:29]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)=[N:30][N:31]=2)=[O:26])[CH2:22]1)(=O)=O>>[CH2:3]1[C:4]2([CH2:7][N:6]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH:21]4[CH2:24][N:23]([C:25]([C:27]5[O:28][C:29]([C:32]6[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=6)=[N:30][N:31]=5)=[O:26])[CH2:22]4)=[CH:11][CH:10]=3)[CH2:5]2)[CH2:1][O:2]1

Participants

3

Reactant 2

HCID 595635064-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenolHCID 595635071-(5-(4-Chlorophenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Product 1

HCID 46937295(3-(4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)methanoneYield 12%

Procedure

The title compound was prepared using a similar protocol as described in Example 1 employing 2A and 2C as starting materials. There was obtained 70 mg (12%) of 2 as an oil. The oil gradually solidified on standing in room temperature. 1H NMR (500 MHz, CDCl3): δ 3.41 (s, 4H), 3.53 (s, 2H), 4.34 (d, 1H), 4.65 (m, 1H), 4.74 (s, 5H), 5.09 (m, 1H), 5.14 (m, 1H), 6.73 (d, 2H), 7.21 (d, 2H), 7.52 (d, 2H), 8.10 (d, 2H), MS (APCI+) m/z 467 [M+H]−, LC purity: 92%.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-551a65bff9954211a0c88b4422ec87fc
Source dataset
uspto-grants-2012_02
Patent number
US08110566B2

Reaction notes

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