1,2-Dichloroethane → HCID 68902323, compound

HRID 1783491Notes

Reaction equation

HRID 1783491 reaction equation
[C:1]1([S:11]([C:14]2[C:19]3[N:20]=[C:21]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[O:22][C:18]=3[CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:29](=O)[CH3:30].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.[Cl:50]CCCl>CO.C(Cl)Cl>[ClH:50].[ClH:50].[CH2:29]([N:26]1[CH2:27][CH2:28][N:23]([C:21]2[O:22][C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([S:11]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)(=[O:13])=[O:12])[C:19]=3[N:20]=2)[CH2:24][CH2:25]1)[CH3:30]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23624309HCID 23624309, compound

Product 1

HCID 68902323HCID 68902323, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(1-naphthylsulfonyl)-2-piperazin-1-ylbenzoxazole (0.070 g, 0.18 mmol), acetaldehyde (0.016 g, 0.36 mmol), NaBH(OAc)3 (0.075 g, 0.36 mmol), and acetic acid (0.021 g, 0.36 mmol) in 1,2-dichloroethane was stirred at room temperature overnight, diluted with 20% MeOH in CH2Cl2 (with 0.5% NH4OH) and filtered through a pad of silica gel. The filtrate was concentrated and purified by Gilson reverse phase HPLC. The purified material was treated with a solution of HCl in ether, stirred at room temperature for 5 minutes and concentrated to dryness to five the title compound (17 mg, 19%), characterized by NMR and mass spectral analyses. MS (ES+) m/e 422 (MH+).

Workup

  1. filtrationfiltered through a pad of silica gel
  2. concentrationThe filtrate was concentrated
  3. custompurified by Gilson reverse phase HPLC
  4. additionThe purified material was treated with a solution of HCl in ether
  5. stirringstirred at room temperature for 5 minutes
  6. concentrationconcentrated to dryness to five the title compound (17 mg, 19%)

Sources & evidence

ORD record
ord-8e9b5aa7a5a744a7a83887a36cbc9113
Source dataset
uspto-grants-2009_03
Patent number
US07501421B2

Reaction notes

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