Ethyl cyanoacetate → Diethyl 2-amino-4-(5-cyano-1-benzofuran-2-yl)-6-methyl-1-[3-(trifluoromethyl)-phenyl]-1,4-dihydro-3,5-pyridinedicarboxylate

HRID 1766352Notes

Reaction equation

HRID 1766352 reaction equation
[CH:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:6]=2[CH:7]=1)=O.[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:15].N1CCCCC1.[CH2:28]([O:30][C:31](=[O:46])[CH:32]=[C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=1)[CH3:34])[CH3:29]>C(O)C>[NH2:15][C:14]1[N:35]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:43])([F:44])[F:45])[CH:37]=2)[C:33]([CH3:34])=[C:32]([C:31]([O:30][CH2:28][CH3:29])=[O:46])[CH:1]([C:3]2[O:4][C:5]3[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:6]=3[CH:7]=2)[C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8082Piperidine2×HCID 128136392-Formylbenzofuran-5-carbonitrileHCID 68427624Ethyl-3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

Product 1

HCID 21110150Diethyl 2-amino-4-(5-cyano-1-benzofuran-2-yl)-6-methyl-1-[3-(trifluoromethyl)-phenyl]-1,4-dihydro-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Formyl-1-benzofuran-5-carbonitrile (157 mg, 0.915 mmol) and ethyl cyanoacetate (103 mg, 0.915 mmol) are dissolved in ethanol (8 ml). Piperidine (2.3 mg, 0.027 mmol) is added, and the reaction mixture is stirred for two hours at room temperature. A solution of Example 1A (253 mg, 0.915 mmol) and piperidine (7.8 mg, 0.091 ml) in ethanol (2 ml) is added, and the reaction mixture is stirred at reflux (95° C.) overnight (18 h). The crude reaction mixture is concentrated in vacuo, dissolved in DMSO (7 ml) and purified by preparative HPLC.

Workup

  1. stirringthe reaction mixture is stirred
  2. temperatureat reflux (95° C.) overnight (18 h)
  3. customThe crude reaction mixture
  4. concentrationis concentrated in vacuo
  5. dissolutiondissolved in DMSO (7 ml)
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f71a03f98ccd4b84b4ed58519f425bc6
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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