4-Chloroaniline → HCID 78322373, compound

HRID 1775663Notes

Reaction equation

HRID 1775663 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]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=2)=[CH:27][S:26][C:25]=1[C:39]([O:41]C)=O.[CH:43](OCC)(OCC)[O:44]CC.ClC1C=CC(N)=CC=1>C(O)(=O)C>[CH3:38][O:37][C:31]1[CH:30]=[C:29]([C:28]2[C:24]3[N:23]=[CH:12][N:7]([C:1]4[CH:2]=[CH:3][C:4]([O:44][CH3:43])=[CH:5][CH:6]=4)[C:39](=[O:41])[C:25]=3[S:26][CH:27]=2)[CH:34]=[CH:33][C:32]=1[O:35][CH3:36]

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 31214Ethyl orthoformateHCID 12128604HCID 12128604, compoundHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78322373HCID 78322373, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(3,4-dimethoxyphenyl)thiophene-2-carboxylate (80 mg, 0.27 mmol), triethyl orthoformate (0.6 ml), 4-chloroaniline (62.5 mg, 0.51 mmol), and acetic acid (0.09 ml) were used to give 14.5 mg (0.04 mmol, 28% yield) of the title compound.

Sources & evidence

ORD record
ord-e1f66dd5b04d41ae99bc7edec8817242
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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