Diisopropylethylamine → HCID 58187942, compound

HRID 1845337Notes

Reaction equation

HRID 1845337 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH:5]([C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[CH:15]=1)[C:10]([OH:12])=O)[OH:6])[CH3:2].Cl.Cl.[CH3:27][C:28]1[N:33]=[CH:32][C:31]([C@H:34]([NH2:36])[CH3:35])=[CH:30][CH:29]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH:5]([C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[CH:15]=1)[C:10]([NH:36][C@@H:34]([C:31]1[CH:32]=[N:33][C:28]([CH3:27])=[CH:29][CH:30]=1)[CH3:35])=[O:12])[OH:6])[CH3:2]

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 58188337HCID 58188337, compoundHCID 67053782(R)-1-(6-Methylpyridin-3-yl)ethan-1-amine dihydrochloride

Product 1

HCID 58187942HCID 58187942, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-(2-(diethylamino)-1-hydroxyethyl)-5-(5-methylpyridin-2-yl)benzoic acid (30 mg, 0.075 mmol) in N,N-dimethylformamide (5 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine dihydrochloride (100 mg, 0.48 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (160 mg, 0.42 mmol) and N,N-diisopropylethylamine (300 μL, 1.7 mmol). The reaction mixture was stirred for 16 hours at 25° C. and purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH]) to afford the title product.

Workup

  1. custompurified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH])

Sources & evidence

ORD record
ord-789471145381489fa2d5b5b6dbdb7690
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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