Diisopropylethylamine → HCID 68247167, compound

HRID 592141Notes

Reaction equation

HRID 592141 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[C:12]1([C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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>CN(C=O)C.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:24][C:21]2[CH:20]=[CH:19][C:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:23][N:22]=2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1050975-Phenyl-2-pyridinamineHCID 1372144-Iodophenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68247167HCID 68247167, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-iodophenyl)acetic acid 53-1 (816 mg, 3.14 mmol), 5-phenylpyridin-2-amine 53-2 (534 mg, 3.14 mmol) and HATU (1.19 g, 3.14 mmol) in DMF (1 mL) was added DIEA (1.57 mL, 9.42 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (50 mL), washed with saturated NaHCO3 aqueous solution, water and brine, dried over Na2SO4, and concentrated by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 40% ethyl acetate in hexane to give 2-(4-Iodophenyl)-N-(5-phenylpyridin-2-yl)acetamide 53-3 as pale yellow solid. MS m/z 415.2 (M+1)

Workup

  1. washwashed with saturated NaHCO3 aqueous solution, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated by rotary evaporation
  4. customThe crude product was purified by silica gel flash chromatography
  5. washeluted with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c9ee8e978afe4d00a18a4ad25fc82188
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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