4-Chloroaniline → HCID 86729807, compound

HRID 1775654Notes

Reaction equation

HRID 1775654 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][C:32]([CH3:35])=[CH:31][CH:30]=2)=[CH:27][S:26][C:25]=1[C:36]([O:38]C)=O.C(OCC)(OCC)OCC.[Cl:50]C1C=CC(N)=CC=1>C(O)(=O)C>[Cl:50][C:4]1[CH:5]=[CH:6][C:1]([N:7]2[C:36](=[O:38])[C:25]3[S:26][CH:27]=[C:28]([C:29]4[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=4)[C:24]=3[N:23]=[CH:12]2)=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 31214Ethyl orthoformateHCID 2759771METHYL 3-AMINO-4-(4-METHYLPHENYL)-THIOPHENE-2-CARBOXYLATEHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 86729807HCID 86729807, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(p -tolyl)thiophene-2-carboxylate (100 mg, 0.40 mmol), triethyl orthoformate (1 ml), 4-chloroaniline (94.4 mg, 0.74 mmol), and acetic acid (0.1 ml) were used to give 48 mg (0.14 mmol, 35% yield) of the title compound.

Sources & evidence

ORD record
ord-9106a28ed015446a808cdc9cdde8e427
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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