4-Ethylaniline → HCID 78320478, compound

HRID 1775620Notes

Reaction equation

HRID 1775620 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.N[C:24]1C(C2C=CC=CC=2)=CS[C:25]=1C(OC)=O.C(OCC)(OCC)OCC.C(C1C=CC(N)=CC=1)C>C(O)(=O)C>[CH2:24]([C:4]1[CH:5]=[CH:6][C:1]([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:10]=3[N:9]=[CH:8]2)=[CH:2][CH:3]=1)[CH3:25]

Participants

6

Reactant 4

HCID 115044-EthylanilineHCID 31214Ethyl orthoformateHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78320478HCID 78320478, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-phenylthiophene-2-carboxylate (50 mg, 0.21 mmol), triethyl orthoformate (0.42 ml), 4-ethylaniline (0.05 ml, 0.39 mmol), and acetic acid (0.05 ml) were used to give 59.5 mg (0.18 mmol, 60% yield) of the title compound.

Sources & evidence

ORD record
ord-885a0551bedd49c4b93a3de53fac2db5
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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