Dimethylacetamide → 4-(3-(2-(2-Fluorophenyl)acetylthioureido)-2-fluorophenoxy)-7-methoxyquinoline-6-carboxylic acid

HRID 1873696Notes

Reaction equation

HRID 1873696 reaction equation
FC1C=C([NH:28][C:29]([NH:31][C:32](=[O:40])[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[S:30])C=CC=1OC1C2C(=CC(OC)=C(C(OC(C)(C)C)=O)C=2)N=CC=1.N[C:42]1[CH:63]=[CH:62][C:45]([O:46][C:47]2[C:56]3[C:51](=[CH:52][C:53]([O:60][CH3:61])=[C:54]([C:57]([OH:59])=[O:58])[CH:55]=3)[N:50]=[CH:49][CH:48]=2)=[C:44]([F:64])[CH:43]=1.[F:65]C(C1C=CC=CC=1)C(SN=C=O)=O.CN(C)C(=O)C>C(O)C.C1(C)C=CC=CC=1>[F:65][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][C:32]([NH:31][C:29](=[S:30])[NH:28][C:43]1[C:44]([F:64])=[C:45]([CH:62]=[CH:63][CH:42]=1)[O:46][C:47]1[C:56]2[C:51](=[CH:52][C:53]([O:60][CH3:61])=[C:54]([C:57]([OH:59])=[O:58])[CH:55]=2)[N:50]=[CH:49][CH:48]=1)=[O:40]

Participants

7

Reactant 4

HCID 31374DimethylacetamideHCID 66916241HCID 66916241, compoundHCID 86650700tert-Butyl 4-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-7-methoxyquinoline-6-carboxylateHCID 866507162-Fluorophenylacetyl thioisocyanate

Product 1

HCID 866507154-(3-(2-(2-Fluorophenyl)acetylthioureido)-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 (1.79 g), 2-fluorophenylacetyl thioisocyanate (1.97 g), and a solvent mixture of N,N-dimethylacetamide (30 mL), toluene (30 mL), and ethanol (6 mL), carboxylic acid 39d was yielded as a crude product (1.89 g, yield: 89%). The crude product was employed in a subsequent reaction without further purification.

Sources & evidence

ORD record
ord-c0a84ccf8bf245d69278f49993035784
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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