(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride → (S)-N-(quinuclidine-8-yl)-2-(dimethylamino)benzoxazole-4-carboxamide

HRID 249832

Reaction equation

HRID 249832 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[O:4][C:5]2[C:6](=[C:8]([C:12]([OH:14])=O)[CH:9]=[CH:10][CH:11]=2)[N:7]=1.Cl.Cl.[NH2:18][C@H:19]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1>>[N:21]12[CH2:20][C@@H:19]([NH:18][C:12]([C:8]3[CH:9]=[CH:10][CH:11]=[C:5]4[O:4][C:3]([N:2]([CH3:1])[CH3:15])=[N:7][C:6]=34)=[O:14])[CH:24]([CH2:25][CH2:26]1)[CH2:23][CH2:22]2

Participants

3

Reactant 2

HCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochlorideHCID 668740302-(Dimethylamino)-1,3-benzoxazole-4-carboxylic acid

Product 1

HCID 52946744(S)-N-(quinuclidine-8-yl)-2-(dimethylamino)benzoxazole-4-carboxamide

Procedure

Following general procedure GP-C1, a mixture of 2-(dimethylamino)benzoxazole-4-carboxylic acid and (S)-(−)-3-aminoquinuclidine dihydrochloride were coupled to provide (S)—N-(quinuclidine-8-yl)-2-(dimethylamino)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-25992f7a45df4c36ba766e2f2ff23c76
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Linked notes

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