4-Chloroaniline → HCID 78321436, compound

HRID 1775638Notes

Reaction equation

HRID 1775638 reaction equation
C1(N2[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)C=CC=CC=1.NC1C(C2C=CC=CC=2[F:35])=CSC=1C(OC)=O.C(OCC)(OCC)OCC.[Cl:50][C:51]1[CH:57]=[CH:56][C:54]([NH2:55])=[CH:53][CH:52]=1>C(O)(=O)C>[Cl:50][C:51]1[CH:57]=[CH:56][C:54]([N:55]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([F:35])[CH:18]=4)[C:10]=3[N:9]=[CH:8]2)=[CH:53][CH:52]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 31214Ethyl orthoformateHCID 533358861325307-27-4HCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78321436HCID 78321436, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(2-fluorophenyl)thiophene-2-carboxylate (50 mg, 0.2 mmol), triethyl orthoformate (0.45 ml), 4-chloroaniline (47.2 mg, 0.37 mmol), and acetic acid (0.05 ml) were used to give 52.1 mg (0.15 mmol, 73.0% yield) of the title compound.

Sources & evidence

ORD record
ord-fc8fd3c7fd17491998b79781a5ff6dd7
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

Loading…