1,1-Dichloroethane → HCID 66899098, compound

HRID 550806Notes

Reaction equation

HRID 550806 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)[C:12]3[CH2:17][S:16](=[O:19])(=[O:18])[CH2:15][C:13]=3[N:14]=2)=[C:4]([F:27])[CH:3]=1.Cl.[NH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(O)(=O)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:20]3[CH2:25][CH2:24][CH:23]([NH:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:22][CH2:21]3)[C:12]3[CH2:17][S:16](=[O:19])(=[O:18])[CH2:15][C:13]=3[N:14]=2)=[C:4]([F:27])[CH:3]=1.[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:20]3[CH2:21][CH2:22][CH:23]([N:29]4[CH2:30][CH2:31][CH2:32][C:33]4=[O:35])[CH2:24][CH2:25]3)[C:12]3[CH2:17][S:16](=[O:18])(=[O:19])[CH2:15][C:13]=3[N:14]=2)=[C:4]([F:27])[CH:3]=1

Participants

9

Reactant 5

HCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 67197393HCID 67197393, compound

Product 2

HCID 66899098HCID 66899098, compoundHCID 67197284HCID 67197284, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 230 mg of 1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-one, 140 mg of ethyl 4-aminobutyrate hydrochloride, 0.1 ml of acetic acid, 5 ml of dichloroethane, and 5 ml of DMF was stirred at ambient temperature for 1 hour, here was then added 353 mg of sodium triacetoxyborohydride, and the mixture was stirred at ambient temperature for 19 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, the mixture was extracted twice with chloroform, the organic phase was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by silica-gel column chromatography (chloroform-MeOH) to yield 128 mg of ethyl 4-({1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl}amino)butanoate and 91 mg of 1-{1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl}pyrrolidin-2-one. Recrystallization of the latter from EtOH gave 65 mg of 1-{1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl}pyrrolidin-2-one as colorless solid.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 19 hours
  2. extractionthe mixture was extracted twice with chloroform
  3. washthe organic phase was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica-gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record
ord-6df4cb80daaf4065ad6185c1936a0f2f
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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