Benzo(b)thiophene-2-carboxylic acid → N-[3-cyano-4-(4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl)phenyl]benzo[b]thiophene-2-carboxamide

HRID 2216421Notes

Reaction equation

HRID 2216421 reaction equation
[S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([N:22]2[CH2:27][CH2:26][N:25]([CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH2:24][CH2:23]2)=[C:18]([CH:21]=1)[C:19]#[N:20]>>[C:19]([C:18]1[CH:21]=[C:14]([NH:13][C:6]([C:5]2[S:1][C:2]3[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=3[CH:4]=2)=[O:8])[CH:15]=[CH:16][C:17]=1[N:22]1[CH2:27][CH2:26][N:25]([CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH2:24][CH2:23]1)#[N:20]

Participants

3

Reactant 2

HCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 219423235-amino-2-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]benzonitrile

Product 1

HCID 21942380N-[3-cyano-4-(4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl)phenyl]benzo[b]thiophene-2-carboxamideYield 64.1%

Procedure

By the reaction and treatment in the same manner as in Example 6 using benzo[b]thiophene-2-carboxylic acid (0.4 g) and 5-amino-2-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]benzonitrile (0.6 g), the title compound (0.6 g) was obtained. melting point: >285° C.

Sources & evidence

ORD record
ord-249bb8c699ed493fb41a07ff118ca139
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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