4-Methylmorpholine → N-(2-((tert-butyldimethylsilyloxy)methyl)-4-methoxyphenyl)-3,3,3-trifluoropropanamide

HRID 2201493Notes

Reaction equation

HRID 2201493 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=1[NH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:19][C:20]([F:26])([F:25])[CH2:21][C:22](O)=[O:23].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[Si:1]([O:8][CH2:9][C:10]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=1[NH:12][C:22](=[O:23])[CH2:21][C:20]([F:26])([F:25])[F:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27779723,3,3-Trifluoropropionic acidHCID 669800812-((Tert-butyldimethylsilyloxy)methyl)-4-methoxyaniline

Product 1

HCID 66980120N-(2-((tert-butyldimethylsilyloxy)methyl)-4-methoxyphenyl)-3,3,3-trifluoropropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture of 2-((tert-butyldimethylsilyloxy)methyl)-4-methoxyaniline (14.0 g), 3,3,3-trifluoro-propionic acid (7.30 g, 57.0 mmol), EDCI (15.0 g, 76.5 mmol), HOBT (11.0 g, 80.2 mmol) and NMM (22 mL, 157 mmol) in anhydrous CH2Cl2 (200 mL) was stirred at 20° C. for 2 hours. The mixture was diluted with CH2Cl2 (100 mL), the organic layer was washed with 1M HCl (100 mL), H2O (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated to give the product.

Workup

  1. washthe organic layer was washed with 1M HCl (100 mL), H2O (100 mL) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give the product

Sources & evidence

ORD record
ord-499a93dc1a4c46e28b623616dd12dd63
Source dataset
uspto-grants-2016_06
Patent number
US09364481B2

Reaction notes

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