Ethylamine → HCID 18711877, compound

HRID 1947640Notes

Reaction equation

HRID 1947640 reaction equation
CN(C(O[N:9]1N=N[C:11]2C=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:27]=1[C:28]([OH:30])=O.C(N(C(C)C)CC)(C)C.C(N)C>C(#N)C.C1COCC1>[Br:25][C:26]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:27]=1[C:28]([NH:9][CH2:10][CH3:11])=[O:30]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 2430252-Bromo-5-nitrobenzoic 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 18711877HCID 18711877, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of HATU (501 mg, 1.32 mmol), 2-bromo-5-nitrobenzoic acid (325 mg, 1.32 mmol) and diisopropyl ethylamine (642 μl, 3.90 mmol) in anhydrous acetonitrile (20 ml) at room temperature was added ethylamine (725 μl of a 2.0M solution in THF, 1.45 mmol) and the reaction stirred for 15 hrs. The solvent was evaporated in vacuo and the crude residue purified by flash column chromatography (20% ethyl acetate in petroleum ether) to afford the title compound as a pale yellow solid (155 mg, 43%). HPLC retention time 3.72 min. Mass spectrum (ES+) m/z 273 (M+H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude residue purified by flash column chromatography (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-1014067488974fd6bafe30e43112ca60
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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