Diisopropylethylamine → HCID 67055325, compound

HRID 602987Notes

Reaction equation

HRID 602987 reaction equation
[NH:1]1[CH2:4][CH:3]([CH:5]([C:10]2[CH:11]=[C:12]([CH:18]=[C:19]([F:21])[CH:20]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]([F:9])([CH3:8])[CH3:7])[CH2:2]1.Br[CH:23]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]#[N:28].CCN(C(C)C)C(C)C>C(#N)C>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH:23]([C:24]2[CH:31]=[CH:30][CH:29]=[C:26]([C:27]#[N:28])[CH:25]=2)[N:1]2[CH2:4][CH:3]([CH:5]([C:10]3[CH:11]=[C:12]([CH:18]=[C:19]([F:21])[CH:20]=3)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]([F:9])([CH3:8])[CH3:7])[CH2:2]2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 670553513-[Bromo(4-chlorophenyl)methyl]benzonitrileHCID 67055353Ethyl 3-(1-azetidin-3-yl-2-fluoro-2-methylpropyl)-5-fluorobenzoate

Product 1

HCID 67055325HCID 67055325, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 4.90 g (16.40 mmol) of ethyl 3-(1-azetidin-3-yl-2-fluoro-2-methylpropyl)-5-fluorobenzoate, 8.17 g of 3-[bromo(4-chlorophenyl)methyl]benzonitrile, 6 mL(34.36 mmol) of DIEA in 40 mL of acetonitrile was refluxed for 4 h, then concentrated in vacuo. The mixture was poured into 150 mL of CH2Cl2 and 30 mL of aq NaHCO3. The organic layer was dried over Na2SO4 and concentrated. Two pairs of racemic compounds were separated by silica gel chromatography. Single diastereomers were separated by a chiral AD column; Mass Spectrum: m/e=523 (M+1, 35Cl), 525 (M+1, 37Cl).

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationconcentrated in vacuo
  3. additionThe mixture was poured into 150 mL of CH2Cl2 and 30 mL of aq NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customTwo pairs of racemic compounds were separated by silica gel chromatography
  7. customSingle diastereomers were separated by a chiral AD column

Sources & evidence

ORD record
ord-cb5473dac1ad45ccbdaf58c5f0b59fef
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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