(2-Methoxyethyl)(methyl)amine → (3-(4-(((2-Methoxyethyl)(methyl)amino)methyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone hydrochloride

HRID 1035231Notes

Reaction equation

HRID 1035231 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]2[CH2:13][N:12]([C:14]([C:16]3[O:17][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:19][N:20]=3)=[O:15])[CH2:11]2)=[CH:5][CH:4]=1.[CH3:27][O:28][CH2:29][CH2:30][NH:31][CH3:32]>>[ClH:1].[CH3:27][O:28][CH2:29][CH2:30][N:31]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]2[CH2:13][N:12]([C:14]([C:16]3[O:17][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:19][N:20]=3)=[O:15])[CH2:11]2)=[CH:5][CH:4]=1)[CH3:32]

Participants

3

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 58043149(3-(4-(Chloromethyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

Product 1

HCID 66655908(3-(4-(((2-Methoxyethyl)(methyl)amino)methyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone hydrochloride

Procedure

Using a similar protocol as described in Example 60 employing 60B (0.16 g, 0.41 mmol) and 2-methoxy-N-methylethanamine (0.037 g, 0.41 mmol) as starting materials afforded the desired compound in neutral form as a gum. The residue was then dissolved in MeOH (2 ml) whereupon HCl in MeOH (1.25 M, 2 ml) was added. After a little while, it was evaporated to dryness. The residue was triturated with MeOH/diethyl ether. There was obtained 0.16 g (80%) of 61 as a solid. 1H NMR (500 MHz, DMSO-d6): δ 2.64 (s, 3H), 3.15 (m, 1H), 3.23 (m, 1H), 3.27 (s, 3H), 3.73 (m, 2H), 3.98 (m, 1H), 4.25 (dd, 1H), 4.34 (dd, 1H), 4.47 (m, 2H), 4.68 (m, 1H), 5.15 (m, 1H), 7.35 (d, 2H), 7.5-7.7 (m, 5H), 8.04 (d, 2H), 11.0 (m, 1H), MS (APCI+) m/z 439 [M+H]+, LC purity: 88%.

Sources & evidence

ORD record
ord-9ba23dbad0bb4b12bedd8aef0a22ef8f
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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