Hydrochloric Acid → HCID 86600351, compound

HRID 1942834Notes

Reaction equation

HRID 1942834 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:12]([NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=O)=[CH:20][CH:19]=1)=[O:13].[NH2:29][OH:30].[OH-].[Na+].Cl>CO.C1COCC1>[OH:30][NH:29][C:22](=[O:24])[C:21]1[CH:26]=[CH:27][C:18]([O:17][CH2:16][CH2:15][NH:14][C:12]([C:4]2[O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:3]=2[N:2]([CH3:1])[CH3:28])=[O:13])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 66688396Methyl 4-[2-(3-dimethylaminobenzofuran-2-ylcarbonylamino)ethoxy]benzoate

Product 1

HCID 86600351HCID 86600351, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude methyl 4-[2-(3-dimethylaminobenzofuran-2-yl-carbonylamino)-ethoxy]-benzoate in MeOH and THF was added excess aqueous hydroxylamine solution and NaOH (aq.) to give pH 10-11. The reaction mixture was stirred overnight and then neutralized to pH 7-8 with aqueous hydrochloric acid and concentrated in vacuo. The residue was dissolved in acetonitrile and water and purified with prep HPLC to give the title compound (107 mg). 1H NMR (400 MHz, DMSO-d6) δ 9.88 (m, 1H), 9.31 (t, J=6.0 Hz, 1H), 8.04 (d, J=7.6 Hz, 1H), 7.70 (m, 3H), 7.57 (t, J=7.6 Hz, 1H), 7.45 (t, J=7.6 Hz, 1H), 6.99 (d, J=9.2 Hz, 2H), 4.76 (d, J=4.8 Hz, 2H), 4.23 (t, J=6.0 Hz, 2H), 3.71 (m, 2H), 2.84 (s, 3H), 2.83 (s, 3H). EM (calc.): 397.2; MS (ESI) m/e (M+1H)+: 398.1, (M−1H)−: 396.2.

Workup

  1. customto give pH 10-11
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in acetonitrile
  4. customwater and purified with prep HPLC

Sources & evidence

ORD record
ord-8addfd9dfab844738f6bbb31fa454286
Source dataset
uspto-grants-2013_03
Patent number
US08389570B2

Reaction notes

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