Ethyl orthoformate → HCID 78323318, compound

HRID 1775681Notes

Reaction equation

HRID 1775681 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]1[C:28](C2C=CC=CC=2)=CS[C:25]=1[C:35](OC)=O.C(OCC)(OCC)OCC.[C@H]1(N)C2C(=CC=CC=2)CCC1>C(O)(=O)C>[C:17]1([C:16]2[C:10]3[N:9]=[CH:8][N:7]([C@H:1]4[C:6]5[C:5](=[CH:28][CH:24]=[CH:25][CH:35]=5)[CH2:4][CH2:3][CH2:2]4)[C:12](=[O:13])[C:11]=3[S:14][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 70580721-Aminotetralin, (R)-HCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78323318HCID 78323318, compoundYield 47.6%

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), (R)-1,2,3,4-tetrahydronaphthalen-1-amine (0.141 ml, 0.99 mmol), and acetic acid (0.1 ml) were used to give 73.3 mg (0.20 mmol, 47.6% yield) of the title compound.

Sources & evidence

ORD record
ord-1c9f4de4a99441028954a6b474775cd4
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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