Triethylamine → HCID 70098140, compound

HRID 2368313Notes

Reaction equation

HRID 2368313 reaction equation
[N+:1]([C:4]1[CH:12]=[N:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[NH2:13][CH2:14][C:15]([CH3:18])([OH:17])[CH3:16].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[OH:17][C:15]([CH3:18])([CH3:16])[CH2:14][NH:13][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][N:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27629243-nitroisonicotinic acid

Product 1

HCID 70098140HCID 70098140, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-nitroisonicotinic acid (1.75 g, 10.1 mmol), 1-amino-2-methylpropan-2-ol (968 ul, 10.1 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (4.86 g, 15.1 mmol) and triethylamine (4.9 ml, 35.3 mmol) in tetrahydrofurane (60 ml) was stirred over the week-end at rt. The reaction mixture was diluted with ethyl acetate, washed with water, with brine, dried with magnesium sulfate and concentrated. The crude product was purified by silica gel chromatography using a CH2Cl2/MeOH gradient as eluent, providing the title compound as off-white solid (255 mg, 11%).

Workup

  1. washwashed with water, with brine
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5cf051f0feb1443fae9dedfe6e0ce985
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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