Diisopropylethylamine → HCID 68379549, compound

HRID 1410042Notes

Reaction equation

HRID 1410042 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]([CH3:11])[C:7](=[O:12])[CH:6]=1.[CH3:13][C:14]1([CH3:30])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=2)[O:15]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:11][N:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][NH:2][C:25](=[O:26])[C:24]2[CH:23]=[CH:22][C:21]([B:16]3[O:17][C:18]([CH3:19])([CH3:20])[C:14]([CH3:30])([CH3:13])[O:15]3)=[CH:29][CH:28]=2)=[CH:6][C:7]1=[O:12]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 683792224-(2-aminoethyl)-1-methylpyridin-2(1H)-one hydrochloride

Product 1

HCID 68379549HCID 68379549, compoundYield 150.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-aminoethyl)-1-methylpyridin-2(1H)-one hydrochloride (76 mg, 0.4 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (100 mg, 0.4 mmol), HATU (190 mg, 0.5 mmol) and DIEA (260 mg, 2 mmol) in 25 mL of DCM and 5 mL of DMF was stirred at room temperature overnight. The solution was washed with sat NaHCO3 (2×20 mL), brine (2×20 mL), dried over anhydrous sodium sulfate, concentrated under reduce pressure to give crude N-(2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (230 mg) and used for next step without further purification. LC-MS: 383 [M+H]+, tR=1.41 min.

Workup

  1. washThe solution was washed with sat NaHCO3 (2×20 mL), brine (2×20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-92db1e8d120d436596d664df15ec9568
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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