Hydroxyamine hydrochloride → HCID 135974227, compound

HRID 1157769Notes

Reaction equation

HRID 1157769 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]([F:34])=[C:8]2[C:12]([C:13](=[O:33])[C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:25]=[N:24][N:23]=4)[CH2:18][CH2:17]3)=[O:15])=[CH:11][NH:10][C:9]=12)(=O)[CH3:2].Cl.[NH2:36][OH:37]>CCO>[F:34][C:7]1[CH:6]=[N:5][C:4](/[C:1](=[N:36]/[OH:37])/[CH3:2])=[C:9]2[NH:10][CH:11]=[C:12]([C:13](=[O:33])[C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:25]=[N:24][N:23]=4)[CH2:18][CH2:17]3)=[O:15])[C:8]=12

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 49770160HCID 49770160, compound

Product 1

HCID 135974227HCID 135974227, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-(7-acetyl-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (0.05 g, 0.11 mmol) in EtOH (10 mL) was added hydroxylamine hydrochloride (0.04 g, 0.58 mmol). The mixture was heated to reflux for 1 h, and was then cooled to rt, and concentrated in vacuo. The residue was diluted with MeOH, and the solids that formed were collected and washed with water. The title compound was isolated as an off-white solid (0.027 g). LCMS: m/e 478.5 (M+H)+, ret time 1.53 min (method 1). 1H NMR (500 MHz, DMSO-D6) δ ppm 11.95 (s, 1H) 11.61 (s, 1H) 8.34 (d, J=1.83 Hz, 1H) 8.30 (d, J=3.36 Hz, 1H) 7.56-7.71 (m, 5H) 3.68-3.72 (m, 2H) 3.43-3.48 (m, 2H) 3.30-3.34 (m, 2H) 3.13-3.17 (m, 2H) 2.35 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with MeOH
  5. customthe solids that formed
  6. customwere collected
  7. washwashed with water

Sources & evidence

ORD record
ord-fb2d13e0233341889bc7a6440f325026
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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