2'-Methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acid → 2,3,5,6,7,8-Hexahydro-1'-methyl-5-(2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl)spiro[furo[2,3-g]quinoline-3,4'-piperidine]

HRID 1741111Notes

Reaction equation

HRID 1741111 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.[CH3:23][N:24]1[CH2:29][CH2:28][C:27]2([C:41]3[C:32](=[CH:33][C:34]4[CH2:35][CH2:36][CH2:37][NH:38][C:39]=4[CH:40]=3)[O:31][CH2:30]2)[CH2:26][CH2:25]1>>[CH3:23][N:24]1[CH2:29][CH2:28][C:27]2([C:41]3[C:32](=[CH:33][C:34]4[CH2:35][CH2:36][CH2:37][N:38]([C:20]([C:17]5[CH:16]=[CH:15][C:14]([C:3]6[CH:4]=[CH:5][C:6]([C:8]7[O:9][C:10]([CH3:13])=[N:11][N:12]=7)=[CH:7][C:2]=6[CH3:1])=[CH:19][CH:18]=5)=[O:21])[C:39]=4[CH:40]=3)[O:31][CH2:30]2)[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 186900662'-Methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acidHCID 221158852,3,5,6,7,8-Hexahydro-1'-methylspiro[furo[2,3-g]quinoline-3,4'-piperidine]

Product 1

HCID 218337902,3,5,6,7,8-Hexahydro-1'-methyl-5-(2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl)spiro[furo[2,3-g]quinoline-3,4'-piperidine]

Procedure

The title compound was prepared from 2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acid (D11) and 2,3,5,6,7,8-hexahydro-1'-methylspiro[furo[2,3-g]quinoline-3,4'-piperidine] (D10) using a similar procedure to Example 1 as a white solid (62%). This was converted to its oxalate salt which was obtained as a white solid (mp 187-188° C.) and hydrochloride salt (mp 176-180° C.).

Sources & evidence

ORD record
ord-a71a389ed460438f8a7f42782750a1cc
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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