Tetrahydrofuran → HCID 86655404, compound

HRID 2190475Notes

Reaction equation

HRID 2190475 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.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=1[C:32]([C:35]#[N:36])([CH3:34])[CH3:33].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][C:23]([Cl:22])=[C:24]([C:32]([C:35]#[N:36])([CH3:33])[CH3:34])[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 65578Oxalyl chlorideHCID 668104254-Chloro-3-(1-cyano-1-methylethyl)benzoic acidHCID 86655397N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]acetamide

Product 1

HCID 86655404HCID 86655404, compoundYield 42%

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), 4-chloro-3-(1-cyano-1-methylethyl)benzoic acid (240 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 (112 mg, 42%) was obtained as a colorless solid.

Sources & evidence

ORD record
ord-7c79c7670b724df1874643dfa7449f5c
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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