tert-Butyl 4-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-7-methoxyquinoline-6-carboxylate → 4-Trifluoromethylphenylacetyl isothiocyanate

HRID 1873702Notes

Reaction equation

HRID 1873702 reaction equation
FC1C=C(NC(NC(=O)CC2C=CC=CC=2)=S)C=CC=1OC1C2C(=CC(OC)=C(C(OC(C)(C)C)=O)C=2)N=CC=1.[F:41][C:42]1[CH:64]=[C:63]([NH:65][C:66]([NH:68][C:69](=[O:81])[CH2:70][C:71]2[CH:76]=[CH:75][C:74]([C:77]([F:80])([F:79])[F:78])=[CH:73][CH:72]=2)=[S:67])[CH:62]=[CH:61][C:43]=1[O:44][C:45]1[C:54]2[C:49](=[CH:50][C:51]([O:59][CH3:60])=[C:52]([C:55]([NH:57][CH3:58])=[O:56])[CH:53]=2)[N:48]=[CH:47][CH:46]=1>>[NH2:65][C:63]1[CH:62]=[CH:61][C:43]([O:44][C:45]2[C:54]3[C:49](=[CH:50][C:51]([O:59][CH3:60])=[C:52]([C:55]([NH:57][CH3:58])=[O:56])[CH:53]=3)[N:48]=[CH:47][CH:46]=2)=[C:42]([F:41])[CH:64]=1.[F:80][C:77]([F:78])([F:79])[C:74]1[CH:75]=[CH:76][C:71]([CH2:70][C:69]([N:68]=[C:66]=[S:67])=[O:81])=[CH:72][CH:73]=1

Participants

4

Reactant 2

HCID 86650700tert-Butyl 4-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-7-methoxyquinoline-6-carboxylateHCID 866507204-(2-Fluoro-4-(3-(2-(4-trifluoromethylphenyl)acetyl)thioureido)phenoxy)-7-methoxy-N-methylquinoline-6-carboxamide

Product 2

HCID 621161214-Trifluoromethylphenylacetyl isothiocyanateHCID 669163504-(4-amino-2-fluorophenoxy)-7-methoxy-N-methylquinoline-6-carboxamide

Procedure

Similar to the synthesis of compound 1d, from compound 46a (50.0 mg) and 4-trifluoromethylphenylacetyl isothiocyanate (53.9 mg), the titled compound 47 was yielded (41.2 mg, yield: 48%).

Sources & evidence

ORD record
ord-5cbad82573c843398017ca9059943713
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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