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

HRID 1741112Notes

Reaction equation

HRID 1741112 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[S: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]([OH:22])=O)=[CH:16][CH:15]=1.[CH3:23][N:24]1[CH2:29][CH2:28][C:27]2([C:40]3[C:32](=[CH:33][C:34]4[CH2:35][CH2:36][NH:37][C:38]=4[CH:39]=3)[O:31][CH2:30]2)[CH2:26][CH2:25]1>>[CH3:23][N:24]1[CH2:25][CH2:26][C:27]2([C:40]3[C:32](=[CH:33][C:34]4[CH2:35][CH2:36][N:37]([C:20]([C:17]5[CH:18]=[CH:19][C:14]([C:3]6[CH:4]=[CH:5][C:6]([C:8]7[S:9][C:10]([CH3:13])=[N:11][N:12]=7)=[CH:7][C:2]=6[CH3:1])=[CH:15][CH:16]=5)=[O:22])[C:38]=4[CH:39]=3)[O:31][CH2:30]2)[CH2:28][CH2:29]1

Participants

3

Reactant 2

HCID 106579521'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine]HCID 21833788HCID 21833788, compound

Product 1

HCID 218337911'-Methyl-5-(2'-methyl-4'-(5-methyl-1,3,4-thiadiazol-2-yl) biphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

Procedure

Crude 2'-methyl-4'-(5-methyl-1,3,4-thiadiazol-2-yl)biphenyl-4-carboxylic acid (D73, 500 mg) and 1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (D8) afforded the title compound according to the general method of Example 1. Preparative HPLC afforded 10 mg of pure compound.

Sources & evidence

ORD record
ord-46dc498ee50c44779813ab4dc3122555
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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