4,5,6,7-Tetrahydro-1-benzothiophene-3-carboxylic acid → N-[3-cyano-4-(2,2-dimethyl-3-hydroxypropoxy)phenyl]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 2216426Notes

Reaction equation

HRID 2216426 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[C:3]2[CH2:9][CH2:10][CH2:11][CH2:12][C:2]1=2.Cl.[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH2:24][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27])=[C:19]([CH:22]=1)[C:20]#[N:21]>C(N(CC)CC)C>[C:20]([C:19]1[CH:22]=[C:15]([NH:14][C:6]([C:4]2[C:3]3[CH2:9][CH2:10][CH2:11][CH2:12][C:2]=3[S:1][CH:5]=2)=[O:8])[CH:16]=[CH:17][C:18]=1[O:23][CH2:24][C:25]([CH3:28])([CH3:29])[CH2:26][OH:27])#[N:21]

Participants

4

Reactant 2

HCID 7677384,5,6,7-Tetrahydro-1-benzothiophene-3-carboxylic acidHCID 219423175-Amino-2-(2,2-dimethyl-3-hydroxypropoxy)benzonitrile monohydrochloride

Product 1

HCID 21942378N-[3-cyano-4-(2,2-dimethyl-3-hydroxypropoxy)phenyl]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideYield 58.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

By the reaction and treatment in the same manner as in Example 6 using 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (0.78 g) and 5-amino-2-(2,2-dimethyl-3-hydroxypropoxy)benzonitrile monohydrochloride (1.0 g) and triethylamine (0.6 ml), the title compound (0.87 g) was obtained. melting point: 148-150° C.

Sources & evidence

ORD record
ord-b1c09f302a7b41dd9c3505936ce9602b
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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