Diethylamine → HCID 57969167, compound

HRID 1483666Notes

Reaction equation

HRID 1483666 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=3)=[CH:10][C:5]=2[CH2:4][O:3]1.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22].CCN(C(C)C)C(C)C.C1CN([P+](Cl)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:21]([N:23]([CH2:24][CH3:25])[C:16](=[O:18])[C:15]1[CH:19]=[CH:20][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:6]3[B:2]([OH:1])[O:3][CH2:4][C:5]=3[CH:10]=2)=[N:13][CH:14]=1)[CH3:22]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 16211753Chlorotri(1-pyrrolidinyl)phosphonium hexafluorophosphateHCID 46884278HCID 46884278, compound

Product 1

HCID 57969167HCID 57969167, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 6-(1-Hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)nicotinic acid (0.813 g, 3 mmol) in anhydrous DMF (70 mL) was added diethylamine (3.2 mL, 30 mmol) and DIPEA (1.6 mL, 9 mmol) under N2. The mixture was cooled with ice bath and a coupling agent PyCloP (Aldrich#26564, 1.4 g, 3.3 mmol) was added. The reaction mixture was stirred at 0° C. for 10 min and at room temperature overnight, and then rotary evaporated. The residue was dissolved in EtOAc and washed with water, evaporated and purified by flash column chromatography over silica gel eluted with EtOAc to provide the title amide compound as a white solid (0.92 g, 2.82 mmol, yield 94%).

Workup

  1. temperatureThe mixture was cooled with ice bath
  2. washwashed with water
  3. customevaporated
  4. custompurified by flash column chromatography over silica gel
  5. washeluted with EtOAc

Sources & evidence

ORD record
ord-c9b0080c3073436ca39648530d2223c8
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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