Hydroxylamine → HCID 178513319, compound

HRID 646874Notes

Reaction equation

HRID 646874 reaction equation
[N:1]1([C:7]2[CH:12]=[C:11]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:19][C:20]([C:22]2[O:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=2)=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:29][OH:30]>CCO>[N:1]1([C:7]2[CH:12]=[C:11]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:19][C:20]([C:22]2[O:23][C:24]([C:27](=[NH:28])[NH:29][OH:30])=[CH:25][CH:26]=2)=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 44447253HCID 44447253, compound

Product 1

HCID 178513319HCID 178513319, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-cyano-furan-2-carboxylic acid (2,4-di-piperidin-1-yl-phenyl)-amide (48 mg, 0.12 mmol, as prepared in the previous step) in 1 mL of EtOH at room temperature was added NH2OH (26 mg, 0.4 mmol, 50% wt/H2O) via syringe. The reaction was heated to reflux for 10 min, and then cooled to 0° C. The bright yellow precipitate was filtered, washed with cold 50% EtOH—H2O (2 mL) and dried to afford 11 mg (23%) of the title compound as a bright yellow solid. 1H-NMR (DMSO-d6; 400 MHz): δ 9.83 (s, 1H), 9.37 (s, 1H), 7.84 (d, 1H, J=9.0 Hz), 7.21 (d, 1H, J=3.5 Hz), 6.89 (d, 1H, J=3.6 Hz), 6.74 (s, 1H), 6.66 (d, 1H, J=8.8 Hz), 5.96 (br s, 2H), 3.08-3.10 (m, 4H), 2.78-2.77 (m, 4H), 1.71-1.52 (m, 12H); Mass spectrum (ESI, m/z): Calcd. for C22H29N5O3 412.2 (M+H), found 412.2;

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 10 min
  3. filtrationThe bright yellow precipitate was filtered
  4. washwashed with cold 50% EtOH—H2O (2 mL)
  5. customdried

Sources & evidence

ORD record
ord-f3bfe403a92c4947a127fb7fc95779e2
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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