Diisopropylethylamine → HCID 131736504, compound

HRID 1478195Notes

Reaction equation

HRID 1478195 reaction equation
[NH2:1][C:2]1[C:3](=[O:15])[N:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]([CH3:8])[C:6]=1[CH3:7].[Si:16]([O:23][C@@H:24]([CH3:40])[C@H:25]([C:31]1[O:35][N:34]=[C:33]([C:36](O)=[O:37])[C:32]=1[CH3:39])[O:26][CH2:27][C:28]([CH3:30])=[CH2:29])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Si:16]([O:23][C@@H:24]([CH3:40])[C@H:25]([C:31]1[O:35][N:34]=[C:33]([C:36]([NH:1][C:2]2[C:3](=[O:15])[N:4]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[N:5]([CH3:8])[C:6]=2[CH3:7])=[O:37])[C:32]=1[CH3:39])[O:26][CH2:27][C:28]([CH3:30])=[CH2:29])([C:19]([CH3:22])([CH3:20])[CH3:21])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 612730214-amino-2-cyclohexyl-1,5-dimethyl-2,3-dihydro-1H-pyrazol-3-one2×HCID 125496396HCID 125496396, compound

Product 1

HCID 131736504HCID 131736504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-2-cyclohexyl-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate D) (2.63 g, 12.55 mmol) was added portionwise to 5-((1R,2S)-2-((tert-butyldimethylsilyl)oxy)-1-((2-methylallyl)oxy)propyl)-4-methylisoxazole-3-carboxylic acid (4.14 g, ˜70% w/w) in DMF (100 mL) followed by DIPEA (7.8 ml, 44.8 mmol) and HATU (4.8 g, 12.55 mmol). After stirring at room temperature for 18 h the reaction mixture was partitioned between EtOAc and brine. The aqueous phase was extracted with EtOAc and the combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 50-100% EtOAc in iso-hexane afforded the title compound;

Workup

  1. customwas partitioned between EtOAc and brine
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was adsorbed onto silica and purification by chromatography
  7. washeluting with 50-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-bbdb290ada2a4262981517d83f83ce60
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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