Chloroacetaldehyde → HCID 66580642, compound

HRID 1521836Notes

Reaction equation

HRID 1521836 reaction equation
Cl.[N:2]1([C:8]([C:10]2[C:11]3[CH2:28][S:27](=[O:30])(=[O:29])[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:12]=3[N:13]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:14]=2)=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[Cl:31][CH2:32][CH:33]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[Cl:31][CH2:32][CH2:33][N:18]1[CH2:19][CH2:20][CH:15]([N:13]2[C:12]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[S:27](=[O:30])(=[O:29])[CH2:28][C:11]=3[C:10]([C:8]([N:2]3[CH2:3][CH2:4][O:5][CH2:6][CH2:7]3)=[O:9])=[N:14]2)[CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 33ChloroacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66578872HCID 66578872, compound

Product 1

HCID 66580642HCID 66580642, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 3-(morpholin-4-ylcarbonyl)-1-piperidin-4-yl-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide hydrochloride (100 mg; 0.23 mmol; 1 eq.), chloroacetaldehyde (31.13 mg; 0.24 mmol; 1.1 eq.) in DCE (4.2 ml) is added sodium triacetoxyborohydride (229.27 mg; 1.08 mmol; 1.4 eq) and the reaction mixture is stirred at 65° C. overnight. The reaction mixture is diluted with DCM and the organic phase is washed with a saturated aqueous solution of NaHCO3 then dried on MgSO4 and concentrated. The residue is purified by flash chromatography eluting from 100% to 30% AcOEt and MeOH to afford after concentration of the desired fractions of the title compound as a brown oil. HPLC (max plot) 89.6%; Rt 2.33 min.

Workup

  1. washthe organic phase is washed with a saturated aqueous solution of NaHCO3
  2. customthen dried on MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography
  5. washeluting from 100% to 30% AcOEt and MeOH

Sources & evidence

ORD record
ord-d96d51e556864fa4909d39f1d83f3a5d
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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