1'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine] → 5-(2,3'-Dimethyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1741104Notes

Reaction equation

HRID 1741104 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:18]3[C:10](=[CH:11][C:12]4[CH2:13][CH2:14][NH:15][C:16]=4[CH:17]=3)[O:9][CH2:8]2)[CH2:4][CH2:3]1.[CH3:19][C:20]1[CH:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[CH:22][C:21]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:36][C:37]([CH3:40])=[N:38][N:39]=2)=[C:31]([CH3:41])[CH:30]=1>>[CH3:19][C:20]1[CH:25]=[C:24]([C:26]([N:15]2[C:16]3[CH:17]=[C:18]4[C:5]5([CH2:8][O:9][C:10]4=[CH:11][C:12]=3[CH2:13][CH2:14]2)[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]5)=[O:27])[CH:23]=[CH:22][C:21]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:36][C:37]([CH3:40])=[N:38][N:39]=2)=[C:31]([CH3:41])[CH:30]=1

Participants

3

Reactant 2

HCID 106579521'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine]HCID 218337632,3'-Dimethyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acid

Product 1

HCID 218337155-(2,3'-Dimethyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

Procedure

The title compound was prepared from 1'-methyl-2,3,6,7-tetrahydrospiro [furo[2,3-f]indole-3,4'-piperidine] (D8) and 2,3'-dimethyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acid (D36) using a similar procedure to Example 1 (31%). This was converted to its oxalate salt and crystallised from acetone/methanol as a pale yelloe solid mp. 193-195° C.

Workup

  1. customcrystallised from acetone/methanol as a pale yelloe solid mp. 193-195° C.

Sources & evidence

ORD record
ord-0caeec59b62142ff8db2302da854e7f1
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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