Hydroxyamine hydrochloride → HCID 10310577, compound

HRID 1013063Notes

Reaction equation

HRID 1013063 reaction equation
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[F:9][C:10]([F:38])([F:37])[C:11]1[CH:12]=[C:13]([N:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34](Cl)=[O:35])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1>O1CCCC1.O>[OH:3][NH:2][C:34](=[O:35])/[CH:33]=[CH:32]/[C:29]1[CH:30]=[CH:31][C:26]([S:23]([N:20]2[CH2:21][CH2:22][N:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([C:10]([F:38])([F:37])[F:9])[CH:12]=3)[CH2:18][CH2:19]2)(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 57503233HCID 57503233, compound

Product 1

HCID 10310577HCID 10310577, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of hydroxylamine hydrochloride (0.24 g, 3.4 mmol) in tetrahydrofuran (5.0 mL) a solution of NaHCO3 (0.40 g, 4.8 mmol) in water (6 mL) was added and the resultant mixture was stirred at ambient temperature for 5 minutes. The reaction mixture was added to a suspension of (E)-3-[4-({4-[3-(trifluoromethyl)phenyl]-1-piperazinyl}sulfonyl)phenyl]-2-propenoyl chloride (10a) (0.31 g) in tetrahydrofuran (5 mL) and the mixture was stirred at ambient temperature for 0.5 hours. The mixture was poured into water (25 mL), the precipitate was filtered, washed with water, ether, and dried to give the title compound (0.23 g, 73%). M.p. 178-179° C. 1H NMR (DMSO-d6, HMDSO), δ: 2.95-3.10 (4H, m); 3.23-3.40 (4H, m, overlapped with a signal of water); 6.62 (1H, d, J=15.9 Hz); 7.09 (1H, d, J=7.7 Hz); 7.16 (1H, s); 7.19 (1H, d, J=8.0 Hz); 7.40 (1H, t, J=7.7 Hz); 7.54 (1H, d, J=15.9 Hz); 7.80 (2H, d, J=8.4 Hz); 7.83 (2H, d, J=8.4 Hz); 9.35 (1H, br s); 10.72 (1H, br s). HPLC analysis on Omnispher 5 C18 column: impurities 3.5% (column size 4.6×150 mm; mobile phase acetonitrile-0.1M acetate buffer (pH 5.0), 50:50; sample concentration 1 mg/ml; flow rate 1.3 mL/min; detector UV 254 nm). Anal. Calcd for C20H20F3N3O4S, %: C, 52.74; H, 4.43; N, 9.23; S, 7.04. Found, %: C, 52.04; H, 4.29; N, 8.86; S, 7.20.

Workup

  1. additionwas added
  2. filtrationthe precipitate was filtered
  3. washwashed with water, ether
  4. customdried

Sources & evidence

ORD record
ord-d5032b427a7b4ce8a7caee21ba45d14f
Source dataset
uspto-grants-2011_07
Patent number
US07981895B2

Reaction notes

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