Tetrahydrofuran → N-(3-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)-3-cyanobenzamide

HRID 2190476Notes

Reaction equation

HRID 2190476 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][C:6]1[CH:18]=[CH:17][C:9]2[N:10]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[S:12][C:8]=2[CH:7]=1.[C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](O)=[O:28])#[N:23].O1CCCC1.C(Cl)(=O)C(Cl)=O>CN(C)C=O>[C:14]([NH:13][C:11]1[S:12][C:8]2[CH:7]=[C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:27](=[O:28])[C:26]4[CH:30]=[CH:31][CH:32]=[C:24]([C:22]#[N:23])[CH:25]=4)[CH:21]=[CH:20][CH:19]=3)[CH:18]=[CH:17][C:9]=2[N:10]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 158753-Cyanobenzoic acidHCID 65578Oxalyl chlorideHCID 86655397N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]acetamide

Product 1

HCID 86655405N-(3-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)-3-cyanobenzamideYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Using N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]acetamide (160 mg, 0.534 mmol) produced in Example A40(x), 3-cyanobenzoic acid (157 mg, 1.07 mmol), tetrahydrofuran (4 mL), N,N-dimethylformamide (10 μL), oxalyl chloride (170 mg, 1.34 mmol) and N,N-dimethylformamide (4 mL), and in the same manner as in Example A40(xi), the title compound (127 mg, 55%) was obtained as a colorless solid.

Sources & evidence

ORD record
ord-c996750b9eac4033861c7b6b67e9efdf
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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