(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride → (S)-2-morpholino-N-(quinuclidin-3-yl)benzo[d]oxazole-4-carboxamide

HRID 249833

Reaction equation

HRID 249833 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:8][C:9]3[C:10](=[C:12]([C:16]([OH:18])=O)[CH:13]=[CH:14][CH:15]=3)[N:11]=2)[CH2:3][CH2:2]1.Cl.Cl.[NH2:21][C@H:22]1[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]1>>[N:24]12[CH2:23][C@@H:22]([NH:21][C:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:9]4[O:8][C:7]([N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)=[N:11][C:10]=34)=[O:18])[CH:27]([CH2:28][CH2:29]1)[CH2:26][CH2:25]2

Participants

3

Reactant 2

HCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochlorideHCID 668743972-Morpholinobenzoxazole-4-carboxylic acid

Product 1

HCID 52943305(S)-2-morpholino-N-(quinuclidin-3-yl)benzo[d]oxazole-4-carboxamide

Procedure

Following general procedure GP-C1, a mixture of 2-morpholinobenzoxazole-4-carboxylic acid and (S)-(−)-3-aminoquinuclidine dihydrochloride were coupled to provide (S)—N-(quinuclidine-8-yl)-2-morpholino-benzoxazole-4-carboxamide, which was converted to the hydrochloride salt following general procedure GP-D1. 1H NMR and MS consistent.

Sources & evidence

ORD record
ord-b7681d82640a475f8d793ccd1cab8e34
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Linked notes

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