O-Methylhydroxylamine hydrochloride → HCID 86638398, compound

HRID 545585Notes

Reaction equation

HRID 545585 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[N:18]=[C:19]([CH3:22])[S:20][CH:21]=1)[C:11]1[CH2:10][CH2:9][C@@H:8]([NH:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[CH2:7][C:6]2=1)=O.Cl.[CH3:30][O:31][NH2:32]>N1C=CC=CC=1.O.Cl.CCOC(C)=O>[CH3:30][O:31][N:32]=[CH:1][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[N:18]=[C:19]([CH3:22])[S:20][CH:21]=1)[C:11]1[CH2:10][CH2:9][C@@H:8]([NH:23][C:24](=[O:28])[CH:25]([CH3:26])[CH3:27])[CH2:7][C:6]2=1

Participants

7

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 59161293HCID 59161293, compound

Product 1

HCID 86638398HCID 86638398, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Dissolve (R)-N-[6-formyl-9-(2-methyl-thiazol-4-ylmethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 211) (53 mg, 0.13 mmol) and methoxyamine HCl (22 mg, 0.27 mmol) in pyridine (1 mL). Stir the reaction mixture for 18 h at 25° C. Dilute the reaction mixture with water (2 mL), 1N HCl (1 mL), and EtOAc (10 mL). Load the mixture onto a Varian ChemElut CE1005 solid-phase extraction cartridge (Varian part number 12198006), then elute, collect, and concentrate 50 mL EtOAc to give the crude product (59 mg) as a white solid. Purify on 8 g silica gel (50-60% EtOAc/hexanes) to afford 34 mg (62%) of the title compound as a white solid. MS (ES): m/z 425 (M+1), 469 (M+HCO2−); 1H NMR (CDCl3): δ 8.16 (s, 1H), 7.63 (d, 1H, J=1.3 Hz), 7.44 (dd, 1H, J=8.6, 1.5 Hz), 7.24 (d, 1H, J=8.5 Hz), 6.36 (s, 1H), 5.55 (d, 1H, J=7.9 Hz), 5.29 (td, 2H, J=24.7, 9.0 Hz), 4.41 (m, 1H), 3.96 (s, 3H), 3.13 (dd, 1H, J=15.4, 4.8 Hz), 2.80 (m, 2H), 2.68 (s, 3H), 2.62 (dd, 1H, J=15.6, 6.8 Hz), 2.30 (m, 1H), 2.14-1.97 (m, 2H), 1.14 (d, 6H, J=6.6 Hz).

Workup

  1. extractionLoad the mixture onto a Varian ChemElut CE1005 solid-phase extraction cartridge (Varian part number 12198006)
  2. washelute
  3. customcollect
  4. concentrationconcentrate 50 mL EtOAc
  5. customto give the crude product (59 mg) as a white solid
  6. customPurify on 8 g silica gel (50-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6887b333e079499a9de250e7a7d0492f
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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