Hydroxylamine, N-chloro- → HCID 42613754, compound

HRID 1410286Notes

Reaction equation

HRID 1410286 reaction equation
C[O-].[Na+].[CH2:4]([N:6]([CH2:32][CH3:33])[CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](OC)=[O:19])=[CH:12][C:11]=1[NH:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:5].[OH:34][NH:35]Cl.Cl.CO>CO>[CH2:4]([N:6]([CH2:32][CH3:33])[CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:35][OH:34])=[O:19])=[CH:12][C:11]=1[NH:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:5]

Participants

6

Reactant 4

HCID 149953Hydroxylamine, N-chloro-HCID 10942334Sodium MethoxideHCID 21893726Hydrochloride methanolHCID 67385665HCID 67385665, compound

Product 1

HCID 42613754HCID 42613754, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under stirring, sodium methoxide (30% in methanol; 2.72 g, 15.1 mmol) was added to a methanol (1.6 mL) solution of (E)-methyl 3-(4-(2-(diethylamino)ethylthio)-3-(3-phenylpropylamino)phenyl)acrylate (229 mg, 0.54 mmol) and hydroxylamino hydrochloride (750 mg, 10.8 mmol). The resulted mixture was kept at room temperature for 5-50 min, then a pre-cooled HCl-MeOH solution was added and pH was adjusted to 7. Solvent was removed under reduced pressure. The product was purified by chromatography. 5 mg of (E)-3-(4-(2-(diethylamino)ethylthio)-3-(3-phenylpropylamino)-phenyl)-N-hydroxy-acrylamide (I) was obtained. Yield: 2%. TLC: Rf=0.23 (DCM:MeOH=9:1); HPLC: 93.1%; tR=8.16 min (LC/PDA: Diamonsil C18 5μ 150×4.6 mm, flow rate 1.0 mL/min, grade: 10-100% B, 20 minutes; mobile phase A: H2O; mobile phase B: acetonitrile; UV254); 1HNMR (400 MHz, DMSO-δ6) δ: 10.68 (1H, s), 9.00 (1H, s), 7.17-7.37 (6H, m), 6.77 (1H, d, J=8.0 Hz), 6.72 (1H, s), 6.40 (1H, d, J=16.0 Hz), 5.45 (1H, br), 3.20 (2H, q, J=6.4 Hz), 2.86 (2H, br), 2.69 (3H, t, 8.0 Hz), 1.90 (2H, m, 3.2 Hz), 0.92 (6H, br). MS (m/z): 428 (MH)+.

Workup

  1. customSolvent was removed under reduced pressure
  2. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-6c63d0e51d6c4d459beaeebd74474f50
Source dataset
uspto-grants-2014_12
Patent number
US08921424B2

Reaction notes

Loading…