1,1-Dichloroethane → HCID 9936394, compound

HRID 1276367Notes

Reaction equation

HRID 1276367 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH:11]1[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18](=[O:35])[CH2:19][S:20][C:21]2[N:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[CH:23][N:22]=2)[CH2:12]1.ClC(Cl)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOCC>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:11]1[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18](=[O:35])[CH2:19][S:20][C:21]2[N:22]=[CH:23][C:24]([C:27]3[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)=[CH:25][N:26]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 357452,3-DichlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22115362HCID 22115362, compound

Product 1

HCID 9936394HCID 9936394, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,3-Dichlorobenzaldehyde (115 mg, 0.66 mmol, 1.5 equiv.) was added to N-(pyrrolidin-3-(RS)-ylmethyl)-2-[5-(4-methoxyphenyl)pyrimidin-2-ylthio]acetamide in dichloroethane (3.4 mL, 0.44 mmol). Excess Na(OAc)3BH (0.2 g, 0.9 mmol, ~3 equiv.) was added and the resulting suspension was stirred vigorously overnight. The reaction mixture was diluted with ether and quenched with 1 M hydrochloric acid to afford a cloudy mixture. The organic layer was carefully removed and the aqueous phase made basic with 5 M aqueous sodium hydroxide to pH 11. After thorough extraction with ethyl acetate, the combined organic phases was washed with brine, then dried over sodium sulfate and concentrated. Chromatography on silica (0-10% methanol in ethyl acetate) afforded N-(1-(2,3-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl)-2-[5-(4-methoxyphenyl)pyrimidin-2-ylsulfanyl]acetamide that was converted to the hydrochloride salt using 4 M hydrochloric acid solution in dioxane and ether (60 mg).

Workup

  1. customquenched with 1 M hydrochloric acid
  2. customto afford a cloudy mixture
  3. customThe organic layer was carefully removed
  4. extractionAfter thorough extraction with ethyl acetate
  5. washthe combined organic phases was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a34b6fd293474f2180a584977693fedf
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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