Triethylamine → HCID 86759635, compound

HRID 1814807Notes

Reaction equation

HRID 1814807 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH3:12][C@H:13]1[CH2:18][NH:17][CH2:16][CH2:15][N:14]1[C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22].C(N(CC)CC)C>C(Cl)Cl>[CH3:12][C@H:13]1[CH2:18][N:17]([C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:16][CH2:15][N:14]1[C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:22])[F:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 20773303HCID 20773303, compound

Product 1

HCID 86759635HCID 86759635, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Cyanobenzoyl chloride (0.30 g) was added to a stirred solution of the (R)-[2-(S)-methyl-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (Example 27; 0.40 g) and triethylamine (0.30 ml) in DCM (10 ml). The reaction mixture was allowed to stir at room temperature for 17 hours (overnight), and then partitioned between DCM (20 ml) and 2 M HCl (20 ml). The organic phase was separated, dried and concentrated to give a gum. The residue was purified by chromatography on an 8 g silica Biotage cartridge eluting 1:1 EtOAc/isohexane to give the title compound (0.445 g) as a white solid. NMR (DMSO-d6, 100° C.): 1.17 (d, 3H), 1.58 (s, 3H), 3.05-3.14 (m, 1H), 3.23-3.29 (m, 2H); 3.73 (brs, 1H), 3.88 (brs, 1H), 4.47 (d, 1H), 4.79 (brs, 1H), 6.79 (s, 1H), 7.58 (d, 2H), 7.88 (d, 2H); m/z 368.

Workup

  1. custompartitioned between DCM (20 ml) and 2 M HCl (20 ml)
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. customto give a gum
  6. customThe residue was purified by chromatography on an 8 g silica Biotage cartridge
  7. washeluting 1:1 EtOAc/isohexane

Sources & evidence

ORD record
ord-808d65ebd6bf4bca91d5f7a95a8da798
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

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