Triethylamine → HCID 87134254, compound

HRID 1749157Notes

Reaction equation

HRID 1749157 reaction equation
[C:1]1([C:7]2([CH2:11][C:12]([OH:14])=O)[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:16][NH:17][O:18][CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.O>[CH3:19][O:18][N:17]([CH3:16])[C:12](=[O:14])[CH2:11][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53429106(1-Phenylcyclobutyl)acetic acid

Product 1

HCID 87134254HCID 87134254, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of Example 68C (2.0 g, 10.5 mmol), N,O-dimethylhydroxylamine hydrochloride (1.5 g, 15.8 mmol), HATU (4.8 g, 12.6 mmol) and triethylamine (2.1 g, 21.0 mmol) in 100 mL dichloromethane was stirred at room temperature overnight. The resulting mixture was diluted with water (100 mL) and the aqueous layer was extracted with dichloromethane (50 mL×3). The combined organic layer was dried over Na2SO4, filtered, and concentrated to afford yellow oil. The crude product was purified by reserve-phase C18 column chromatography (H2O/CH3OH=1:4) to afford desired compound (2.2 g, 9.4 mmol, 89.5%) of title compound. LC-MS: m/e=234.1 (M+H+).

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane (50 mL×3)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford yellow oil
  6. customThe crude product was purified by reserve-phase C18 column chromatography (H2O/CH3OH=1:4)

Sources & evidence

ORD record
ord-600fffcf91514aafb52f744ce5a63d84
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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