Acetic Acid → HCID 66744099, compound

HRID 657490Notes

Reaction equation

HRID 657490 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:16]=1)(=[O:14])=[O:13].[C:30](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.[Cl:50]CCl>>[ClH:50].[F:29][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([N:23]2[CH2:28][CH2:27][N:26]([CH3:30])[CH2:25][CH2:24]2)[CH:16]=1)(=[O:13])=[O:14]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 49781603HCID 49781603, compound

Product 1

HCID 66744099HCID 66744099, compound

Procedure

0.429 g N-(2-(difluoromethoxy)-5-methylphenyl)-4-methoxy-3-(piperazin-1-yl)benzenesulfonamide (1.004 mmol) were dissolved in 5 mL of dichloromethane. 0.086 mL of acetic acid (1.505 mmol) and 0.319 g of sodium triacetoxyborohydride (3.01 mmol) were added. After stirring for 10 min, 0.083 mL of aqueous formaldehyde solution (3.01 mmol) were added and the reaction stirred for 72 h at room temperature. The solvents were evaporated and the residue purified via preparative silica gel chromatography (Super Flash cartridge (Interchim)) using a dichloromethane (+0.1% triethylamine) and methanol gradient as eluent. Fractions containing the product were combined, the solvents evaporated, and the product converted to the hydrochloride salt by addition of hydrochloric acid in diethyl ether and subsequent evaporation to dryness (yield 0.169 g of product).

Workup

  1. stirringthe reaction stirred for 72 h at room temperature
  2. customThe solvents were evaporated
  3. customthe residue purified via preparative silica gel chromatography (Super Flash cartridge (Interchim))
  4. additionFractions containing the product
  5. customthe solvents evaporated
  6. additionthe product converted to the hydrochloride salt by addition of hydrochloric acid in diethyl ether and subsequent evaporation to dryness (yield 0.169 g of product)

Sources & evidence

ORD record
ord-ecc48b4b4cb6488d90d3846e5c358d51
Source dataset
uspto-grants-2011_12
Patent number
US08076326B2

Reaction notes

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