Ethyl orthoformate → HCID 78323322, compound

HRID 1775685Notes

Reaction equation

HRID 1775685 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]C=[CH:3][CH:2]=1.[NH2:23][C:24]1C(C2C=CC=CC=2)=CSC=1C(OC)=O.C(OCC)(OCC)OCC.CN1CCC(N)CC1>C(O)(=O)C>[CH3:24][N:23]1[CH2:3][CH2:2][CH: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)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 27375314-Amino-1-methylpiperidineHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78323322HCID 78323322, compoundYield 33.8%

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 (1.0 ml), 1-methylpiperidin-4-amine (0.124 ml, 0.99 mmol), and acetic acid (0.1 ml) were used to give 47.3 mg (0.15 mmol, 33.8% yield) of the title compound.

Sources & evidence

ORD record
ord-36999e4c4dee40028d6efb33a5c99f21
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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