Triethylamine → HCID 56646720, compound

HRID 1428170Notes

Reaction equation

HRID 1428170 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:4][CH:3]=1.[O:19]1[CH:23]=[N:22][N:21]=[C:20]1[CH2:24][CH2:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([CH2:25][CH2:24][C:20]3[O:19][CH:23]=[N:22][N:21]=3)=[CH:27][CH:28]=2)=[O:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 69207909HCID 69207909, compoundHCID 86682820HCID 86682820, compound

Product 1

HCID 56646720HCID 56646720, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2E)-3-[4-(4-fluorophenyl)pyridin-3-yl]prop-2-enoic acid (18.0 g), 4-[2-(1,3,4-oxadiazol-2-yl)ethyl]aniline (14.0 g), triethylamine (14.97 g), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (18.84 g) and dichloromethane (2.5 L) was stirred at room temperature for 17 hr. The reaction mixture was washed successively with water and 1 M aqueous sodium hydroxide solution. Methanol (600 mL) was added thereof, and the mixture was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a solid. The obtained solid was recrystallized with ethanol to give the title compound (25.0 g).

Workup

  1. washThe reaction mixture was washed successively with water and 1 M aqueous sodium hydroxide solution
  2. additionMethanol (600 mL) was added
  3. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto give a solid
  6. customThe obtained solid was recrystallized with ethanol

Sources & evidence

ORD record
ord-4a1b382965b644cb905b5c46608a930c
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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