4-Aminobenzonitrile → HCID 78320797, compound

HRID 1775625Notes

Reaction equation

HRID 1775625 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.[NH2:23][C:24]1C(C2C=CC=CC=2)=CSC=1C(OC)=O.C(OCC)(OCC)OCC.NC1C=CC(C#N)=CC=1>C(O)(=O)C>[O:13]=[C:12]1[N:7]([C:1]2[CH:6]=[CH:5][C:4]([C:24]#[N:23])=[CH:3][CH:2]=2)[CH:8]=[N:9][C:10]2[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][S:14][C:11]1=2

Participants

6

Reactant 4

HCID 133964-AminobenzonitrileHCID 31214Ethyl orthoformateHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78320797HCID 78320797, compoundYield 27%

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 (100 mg, 0.43 mmol), triethyl orthoformate (1 ml), 4-aminobenzonitrile (96 mg, 0.81 mmol), and acetic acid (0.1 ml) were used to give 38 mg (0.12 mmol, 27% yield) of the title compound.

Sources & evidence

ORD record
ord-fa44fbac21164ddd8c6954b43ac79792
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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