Hydroxyamine hydrochloride → HCID 73855085, compound

HRID 2121997Notes

Reaction equation

HRID 2121997 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:35][CH2:36][CH3:37])=[C:8]([N:10]=[C:11]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14](=[O:23])[C:13](=[C:24]3[N:28]([CH2:29]C)[C:27]4[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=4[S:25]3)[S:12]2)[CH:9]=1)(=O)[CH3:2].Cl.[NH2:39][OH:40]>N1C=CC=CC=1>[CH2:16]([N:15]1[C:14](=[O:23])[C:13](=[C:24]2[N:28]([CH3:29])[C:27]3[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=3[S:25]2)[S:12][C:11]1=[N:10][C:8]1[CH:9]=[C:4]([C:1](=[N:39][OH:40])[CH3:2])[CH:5]=[CH:6][C:7]=1[NH:35][CH2:36][CH3:37])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 74052867HCID 74052867, compound

Product 1

HCID 73855085HCID 73855085, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To the product of Example 38 was added hydroxylamine hydrochloride (2 equiv) and pyridine. The resulting mixture was heated at 80° C. for 24 h, cooled, concentrated and chromatographed (TEA-washed silica gel, 0-50% EtOAc/Hex) to give the title compound. 1H-NMR (DMSO-d6): δ 11.07 (1H, s), 7.88 (1H, s), 7.67 (2H, m), 7.53 (1H, d), 7.39 (2H, m), 7.21-7.33 (5H, m), 7.09-7.14 (1H, m), 5.05 (2H, s), 3.92 (2H, q), 3.27 (3H, s), 2.23 (3H, s), 1.03 (3H, t); MS(ESI): 530 (MH+).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customchromatographed
  4. wash(TEA-washed silica gel, 0-50% EtOAc/Hex)

Sources & evidence

ORD record
ord-474f77238c40409c883ab06f22d6b038
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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