Diisopropylethylamine → HCID 131733534, compound

HRID 2284726Notes

Reaction equation

HRID 2284726 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[N:3]=1.[C:10]([N:17]([CH3:23])[C@H:18]([C:20](O)=[O:21])[CH3:19])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C)C=O>[C:8]([C:4]1[N:3]=[C:2]([NH:1][C:20](=[O:21])[CH:18]([N:17]([CH3:23])[C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH3:19])[CH:7]=[CH:6][CH:5]=1)#[CH:9]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 450797916-Ethynylpyridin-2-amine

Product 1

HCID 131733534HCID 131733534, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To 2-amino-6-ethynylpyridine (G55, 203 mg) synthesized according to the method described in WO2012/052451 A1, N-Boc-N-methyl-L-alanine (524 mg), and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.31 g), N,N-diisopropylethylamine (1.2 mL) and N,N-dimethylformamide (4.5 mL) were added at room temperature, and the mixture was stirred at 45° C. for 12 hours. The reaction mixture was cooled on ice, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl (1-((6-ethynylpyridin-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (G56, 180 mg) as white solid.

Workup

  1. additionwere added at room temperature
  2. temperatureThe reaction mixture was cooled on ice
  3. customThe organic layer was separated
  4. washwashed successively with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-55911c60e7a1495b9dca71e368b7e645
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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