Triethylamine → N-(3-Cyano-4-neopentyloxyphenyl)-1-(4-fluorophenyl)pyrrole-3-carboxamide

HRID 1744560Notes

Reaction equation

HRID 1744560 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9]2)=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:21]([CH:24]=1)[C:22]#[N:23].C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>O.CN(C)C=O>[C:22]([C:21]1[CH:24]=[C:17]([NH:16][C:13]([C:10]2[CH:11]=[CH:12][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:9]=2)=[O:15])[CH:18]=[CH:19][C:20]=1[O:25][CH2:26][C:27]([CH3:29])([CH3:28])[CH3:30])#[N:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 178227345-Amino-2-neopentyloxybenzonitrileHCID 222280401-(4-Fluorophenyl)pyrrole-3-carboxylic acid

Product 1

HCID 9886747N-(3-Cyano-4-neopentyloxyphenyl)-1-(4-fluorophenyl)pyrrole-3-carboxamideYield 20.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(4-Fluorophenyl)pyrrole-3-carboxylic acid (2 g), 5-amino-2-neopentyloxybenzonitrile (1.8 g), triethylamine (1.7 g) and diethyl cyanophosphate (1.6 g) were added to dimethylformamide (20 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was added into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous methanol to give the title compound (0.7 g), melting point: 167–169° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. additionn-Hexane was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from hydrous methanol

Sources & evidence

ORD record
ord-db1c3c85f4c04bf98560a3cfe4ba0685
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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