Dichloromethane → HCID 10343819, compound

HRID 549292Notes

Reaction equation

HRID 549292 reaction equation
[OH:1]OS([O-])=O.[K+].C([O-])(=O)C.[O-2:11].[Na+].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]2[S:32][C:31]3[CH:30]=[CH:29][N:28]=[C:27]([N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[C:26]=3[CH:25]=2)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].[Cl:39]CCl>O.C(O)C>[ClH:39].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([C:24]2[S:32][C:31]3[CH:30]=[CH:29][N:28]=[C:27]([N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[C:26]=3[CH:25]=2)(=[O:1])=[O:11])=[CH:19][CH:18]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 23707502Potassium hydroxy sulfite2×HCID 67156830HCID 67156830, compoundHCID 131728846HCID 131728846, compound

Product 1

HCID 10343819HCID 10343819, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Oxone (0.52 g, 0.84 mmol) in water (4 mL), buffered to pH ˜6 with sodium oxide acetate, was added to 2-[(4-tert-butylphenyl)thio]-4-piperazin-1-ylthieno[3,2-c]pyridine (0.42 mmol) in ethanol (30 mL). The mixture was stirred in room temperature for 2 h and more oxone (0.52 g, 0.84 mmol) was added. The reaction was stirred over night. Water was added to the mixture, extraction with dichloromethane (2×20 mL) and the solvent was removed. The products were purified by preparative HPLC. Yield: 41.9 mg (22.0%). 1H NMR (500 MHz, CH3OH-d4) δ ppm 8.38 (s, 1H) 8.05-8.01 (m, 3H) 7.80 (d, J=6.59 Hz, 1H) 7.71-7.69 (m, 2H) 4.15-4.13 (m, 4H) 3.59-3.57 (4H) 1.37-1.33 (m, 9H); LC-MS 416 (M−H)+; Purity (HPLC) 95%.

Workup

  1. stirringThe reaction was stirred over night
  2. customthe solvent was removed
  3. customThe products were purified by preparative HPLC

Sources & evidence

ORD record
ord-fab7cdb9da4d4a2da52e7aff0a8ea638
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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