O-Methylhydroxylamine hydrochloride → HCID 49770162, compound

HRID 1157302Notes

Reaction equation

HRID 1157302 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.[O:36]([NH2:38])[CH3:37]>CCO>[F:34][C:7]1[CH:6]=[N:5][C:4](/[C:1](=[N:38]/[O:36][CH3:37])/[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:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:25]=[N:24][N:23]=4)[CH2:18][CH2:17]3)=[O:15])[C:8]=12

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 49770160HCID 49770160, compound

Product 1

HCID 49770162HCID 49770162, 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 methoxylamine hydrochloride (0.05 g, 0.60 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 a light-yellow solid (0.025g). LCMS: m/e 492.4 (M+H)+, ret time 2.068 min (method 2). 1H NMR (500 MHz, DMSO-D6) δ ppm 12.02 (s, 1 H) 8.36 (d, J=2.14 Hz, 1 H) 8.27 (d, J=3.36 Hz, 1 H) 7.56-7.71 (m, 5 H) 4.13-4.16 (m, 3 H) 3.68-3.73 (m, 2 H) 3.43-3.48 (m, 2 H) 3.29-3.36 (m, 2 H) 3.13-3.18 (m, 2 H) 2.36 (s, 3 H).

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-273097b2ffbd43f5a1d3f0f1bae765d9
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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