Dimethylacetamide → 4-(4-(3-(2-(2,6-Difluorophenyl)acetyl)thioureido)-2-fluorophenoxy)-7-methoxyquinoline-6-carboxylic acid

HRID 1873699Notes

Reaction equation

HRID 1873699 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([NH:28][C:29]([NH:31]C(=O)CC2C=CC=CC=2)=[S:30])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:22][CH3:23])=[C:12]([C:15]([O:17]C(C)(C)C)=[O:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.NC1C=CC(OC2C3C(=CC(OC)=C(C(O)=O)C=3)N=CC=2)=C([F:64])C=1.F[CH:66]([C:73]1[C:78]([F:79])=[CH:77][CH:76]=[CH:75][CH:74]=1)[C:67](SN=C=O)=[O:68].CN(C)C(=O)C>C(O)C.C1(C)C=CC=CC=1>[F:79][C:78]1[CH:77]=[CH:76][CH:75]=[C:74]([F:64])[C:73]=1[CH2:66][C:67]([NH:31][C:29](=[S:30])[NH:28][C:26]1[CH:25]=[CH:24][C:3]([O:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:22][CH3:23])=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=3)[N:8]=[CH:7][CH:6]=2)=[C:2]([F:1])[CH:27]=1)=[O:68]

Participants

7

Reactant 4

HCID 31374DimethylacetamideHCID 66916241HCID 66916241, compoundHCID 86650700tert-Butyl 4-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-7-methoxyquinoline-6-carboxylateHCID 866507182,6-Difluorophenylacetyl thioisocyanate

Product 1

HCID 866507174-(4-(3-(2-(2,6-Difluorophenyl)acetyl)thioureido)-2-fluorophenoxy)-7-methoxyquinoline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Similar to the synthesis of compound 1d, from compound 39c (98 mg), 2,6-difluorophenylacetyl thioisocyanate (128 mg), and a solvent mixture of N,N-dimethylacetamide (1.5 mL), toluene (1.5 mL), and ethanol (300 μL), compound 44a was yielded as a crude product (143 mg, yield: 89%).

Sources & evidence

ORD record
ord-f0ca9b9350ce4742860538ffdfcac617
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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