Isoamyl Alcohol → HCID 57884134, compound

HRID 1818083Notes

Reaction equation

HRID 1818083 reaction equation
F[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:11][CH:12]([CH3:16])[CH2:13][CH2:14][OH:15].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH2:37][CH2:38][NH:39][CH3:40])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH2:37][CH2:38][N:39]([CH3:40])[C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[N:10][C:2]=2[O:15][CH2:14][CH2:13][CH:12]([CH3:16])[CH3:11])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]

Participants

7

Reactant 5

HCID 31260Isoamyl AlcoholHCID 77039N-MethylhomoveratrylamineHCID 960892-Fluoronicotinic acidHCID 3251421Potassium bis(trimethylsilyl)amideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57884134HCID 57884134, compoundYield 0.65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-nicotinic acid (84.7 mg, 0.600 mmol, 3-methyl-butan-1-ol (52.9 mg, 0.600 mmol) and potassium bis(trimethylsilyl)amide (478 mg, 2.40 mmol) were combined in 0.6 mL of N,N-dimethylformamide and subjected to microwave irradiation for 3 minutes at 180° C. [2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-amine (117 mg, 0.600 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (304 mg, 0.800 mmol) was added and the solution was allowed to stir for 16 hours. The mixture was then purified by reverse phase preparative liquid chromatography to yield the pure product (1.5 mg, 0.0039 mmol, 0.65%) ESI-MS m/z calc. 386.2, found 387.4 (M+1)+. Retention time of 2.98 minutes.

Workup

  1. additionwas added
  2. customThe mixture was then purified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-0fbc4c9c0ec14eb8b375f75ca0c754cd
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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