Diisopropylethylamine → HCID 16744927, compound

HRID 603005Notes

Reaction equation

HRID 603005 reaction equation
[NH:1]1[CH2:4][CH:3]([CH:5]([C:10]2[CH:11]=[C:12]([C:17]3[N:18]=[N:19][N:20]([CH3:22])[N:21]=3)[CH:13]=[C:14]([F:16])[CH:15]=2)[C:6]([F:9])([CH3:8])[CH3:7])[CH2:2]1.Br[CH:24]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[C:28]#[N:29].CCN(C(C)C)C(C)C>C(#N)C>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([CH:24]([N:1]2[CH2:2][CH:3]([CH:5]([C:10]3[CH:11]=[C:12]([C:17]4[N:18]=[N:19][N:20]([CH3:22])[N:21]=4)[CH:13]=[C:14]([F:16])[CH:15]=3)[C:6]([F:9])([CH3:8])[CH3:7])[CH2:4]2)[C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]#[N:29])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 670553513-[Bromo(4-chlorophenyl)methyl]benzonitrileHCID 67055393HCID 67055393, compound

Product 1

HCID 16744927HCID 16744927, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 240 mg (0.78 mmol) of 5-[3-(1-azetidin-3-yl-2-fluoro-2-methylpropyl)-5-fluorophenyl]-2-methyl-2H-tetrazole, 530 mg (1.56 mmol) of 3-[bromo(4-chlorophenyl) methyl]benzonitrile, 1.1 mL(6.26 mmol) of DIEA in 8 mL of acetonitrile was heated to reflux for 4 h. Then, it was concentrated. The mixture was poured into 30 mL of CH2Cl2 and 5 mL of aq NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The compounds were purified by silica gel chromatography. Single diastereomers were separated by a chiral AD column; Mass Spectrum: m/e=533 (M+1, 35Cl), 535 (M+1, 37Cl).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. concentrationThen, it was concentrated
  4. additionThe mixture was poured into 30 mL of CH2Cl2 and 5 mL of aq NaHCO3
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe compounds were purified by silica gel chromatography
  8. customSingle diastereomers were separated by a chiral AD column

Sources & evidence

ORD record
ord-a6d1701b518a4928abe0191a6ddcd59e
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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