Hydroxylamine → HCID 3013460, compound

HRID 891014Notes

Reaction equation

HRID 891014 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16]CC)=O)[N:2]=1.[H-].[Na+].[Cl:21][C:22]1[S:23][C:24]([CH2:27]Cl)=[CH:25][CH:26]=1.[NH2:29][OH:30]>CN(C=O)C.CO.O>[Cl:21][C:22]1[S:23][C:24]([CH2:27][N:12]2[C:13]3[CH:1]=[N:2][C:3]([C:14]([NH:29][OH:30])=[O:16])=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 24758Sodium hydrideHCID 105078Ethyl Beta-Carboline-3-CarboxylateHCID 5830792-Chloro-5-(chloromethyl)thiophene

Product 1

HCID 3013460HCID 3013460, compoundYield 58.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 9Hβ-carboline-3-carboxylate (300 mg, 1.25 mmol) in DMF (3 mL) under a nitrogen atmosphere was added NaH (50.0 mg, 60% in mineral oil, 1.25 mmol) portionwise, followed by 2-chloro-5-(chloromethyl)-thiophene (151 μL, 1.25 mmol). The stirring was continued for 21 hours at ambient temperature, water (50 mL) was then added to the mixture. The precipitate was filtered, washed with water and dried to give a solid that was dissolved in methanol (25 mL). To the resulting solution, H2NOH (25 mL, 50 wt. % solution in H2O, 0.38 mol) was added. The suspension was stirred for 4 days at ambient temperature. The mixture was then filtered, and the solid was boiled in methanol (25 mL). After filtration, the desired product (0.26 g, 58%) was obtained. 1H NMR (400 MHz, DMSO-d6): □ 11.28 (1H, s), 9.15 (1H, s), 9.01 (1H, s), 8.81 (1H, s), 8.44 (1H, d, J=8 Hz), 6.94–7.92 (5H, m), 5.99 (2H, s). HRMS (M+H)+ found: 358.0417. Calcd for C17H13N3O2SCl: 358.0417.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customto give a solid
  5. filtrationThe mixture was then filtered
  6. filtrationAfter filtration

Sources & evidence

ORD record
ord-1f20356aea64472f89648736ffe205d2
Source dataset
uspto-grants-2006_02
Patent number
US07001912B2

Reaction notes

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