3-Chloroaniline → HCID 78321437, compound

HRID 1775635Notes

Reaction equation

HRID 1775635 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.C(OCC)(OCC)OCC.[Cl:50]C1C=C(C=CC=1)N>C(O)(=O)C>[Cl:50][C:3]1[CH:2]=[C:1]([N:7]2[C:36](=[O:38])[C:25]3[S:26][CH:27]=[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[F:35])[C:24]=3[N:23]=[CH:12]2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 79323-ChloroanilineHCID 31214Ethyl orthoformateHCID 533358861325307-27-4HCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78321437HCID 78321437, compoundYield 73.6%

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), 3-chloroaniline (75.5 mg, 0.59 mmol), and acetic acid (0.09 ml) were used to give 84 mg (0.24 mmol, 73.6% yield) of the title compound.

Sources & evidence

ORD record
ord-efbec65d4dd147eaa40bae1c248382ce
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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