P-Anisidine → HCID 78321749, compound

HRID 1775644Notes

Reaction equation

HRID 1775644 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C(C2C=CC=C([Cl:35])C=2)=CSC=1C(OC)=O.C([O:47][CH2:48]C)(OCC)OCC.COC1C=CC(N)=CC=1>C(O)(=O)C>[Cl:35][C:21]1[CH:22]=[C:17]([C:16]2[C:10]3[N:9]=[CH:8][N:7]([C:1]4[CH:6]=[CH:5][C:4]([O:47][CH3:48])=[CH:3][CH:2]=4)[C:12](=[O:13])[C:11]=3[S:14][CH:15]=2)[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 31214Ethyl orthoformateHCID 533358892-Thiophenecarboxylic acid, 3-amino-4-(3-chlorophenyl)-, methyl esterHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78321749HCID 78321749, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(3-chlorophenyl)thiophene-2-carboxylate (80 mg, 0.3 mmol), triethyl orthoformate (0.66 ml), p-anisidine (68.5 mg, 0.56 mmol), and acetic acid (0.09 ml) were used to give 84 mg (0.23 mmol, 76% yield) of the title compound.

Sources & evidence

ORD record
ord-65102f8d96bf438db2a2121dddaca0ff
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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