4-Methylmorpholine → HCID 68459274, compound

HRID 2356846Notes

Reaction equation

HRID 2356846 reaction equation
[NH2:1][CH:2]([CH3:28])[C:3]([NH:5][C:6]1[N:7]([C:24]([CH3:27])([CH3:26])[CH3:25])[N:8]=[C:9]([C:11]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:10]=1)=[O:4].[F:29][C:30]1[CH:31]=[C:32]([CH:38]=[C:39]([F:41])[CH:40]=1)[C@H:33]([OH:37])[C:34](O)=[O:35].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>C1COCC1>[C:24]([N:7]1[C:6]([NH:5][C:3](=[O:4])[CH:2]([NH:1][C:34](=[O:35])[CH:33]([C:32]2[CH:38]=[C:39]([F:41])[CH:40]=[C:30]([F:29])[CH:31]=2)[OH:37])[CH3:28])=[CH:10][C:9]([C:11]2([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]2)=[N:8]1)([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6951479Benzeneacetic acid, 3,5-difluoro-α-hydroxy-, (αS)-HCID 68457327HCID 68457327, compound

Product 1

HCID 68459274HCID 68459274, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.14 g (0.4 mmol) of 2-amino-N-[2-tert-butyl-5-(1-methyl-4-phenylpiperidin-4-yl)-2H-pyrazol-3-yl]propionamide and 0.08 g (0.4 mmol) of (S)-3,5-difluoromandelic acid (Garofalo, et al. Bioorg. Med. Chem. Lett. 2002, 12, 3051) in 5.0 mL of THF was stirred at rt as 0.06 g (0.4 mmol) of HOBT and 0.08 mL (0.7 mmol) of NMM was added followed by 0.90 g (0.5 mmol) of EDC.HCl. After 16 h, the reaction was quenched with 1M HCl and extracted with EtOAc. The organic layer washed with sat. aq. NaHCO3, dried over MgSO4 and concentrated. Purification on silica gel using 4% Et3N-MeOH as eluant afforded N-[2-tert-butyl-5-(1-methyl-4-phenylpiperidin-4-yl)-2H-pyrazol-3-yl]-2-[2-(3,5-difluorophenyl)-2-hydroxyacetylamino]propionamide.

Workup

  1. additionwas added
  2. customthe reaction was quenched with 1M HCl
  3. extractionextracted with EtOAc
  4. washThe organic layer washed with sat. aq. NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification on silica gel using 4% Et3N-MeOH as eluant

Sources & evidence

ORD record
ord-45a5bac281f64693bdd22e2c926f55b2
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

Loading…