m-Toluidine → HCID 78321118, compound

HRID 1775634Notes

Reaction equation

HRID 1775634 reaction equation
[C:1]1([N:7]2[C:12](=O)C3SC=C(C4C=CC=CC=4)C=3N=C2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][C:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])=[CH:27][S:26][C:25]=1[C:36]([O:38]C)=O.[CH:40](OCC)(OCC)OCC.NC1C=CC=C(C)C=1>C(O)(=O)C>[F:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:28]1[C:24]2[N:23]=[CH:12][N:7]([C:1]3[CH:2]=[C:3]([CH3:40])[CH:4]=[CH:5][CH:6]=3)[C:36](=[O:38])[C:25]=2[S:26][CH:27]=1

Participants

6

Reactant 4

HCID 7934m-ToluidineHCID 31214Ethyl orthoformateHCID 533358861325307-27-4HCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78321118HCID 78321118, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(2-fluorophenyl)thiophene-2-carboxylate (80 mg, 0.3 mmol), triethyl orthoformate (0.79 ml), m-toluidine (63.8 mg, 0.59 mmol), and acetic acid (0.09 ml) were used to give 70 mg (0.21 mmol, 65.0% yield) of the title compound.

Sources & evidence

ORD record
ord-e81c1cbfeb6c4c6eacf894c8d0381e96
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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