1,2-Dichloroethane → HCID 68678753, compound

HRID 1444719Notes

Reaction equation

HRID 1444719 reaction equation
O=[CH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:31])[CH2:13][CH:14]2[C:19](=[O:20])[NH:18][CH:17]=[CH:16][N:15]2[S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:7][CH:6]=1.C(Cl)CCl.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl>[O:20]=[C:19]1[NH:18][CH:17]=[CH:16][N:15]([S:21]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[CH:14]1[CH2:13][C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:6][CH:7]=1)=[O:31]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 76826756HCID 76826756, compound

Product 1

HCID 68678753HCID 68678753, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 20 mL flask equipped with stirring was added N-[4-(3-oxo-propyl)-phenyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide (45 mg, 0.102 mmol), ClCH2CH2Cl (2 mL), piperidine (Aldrich, 0.02 mL, 0.204 mmol) and one drop of HOAc. NaBH(OAc)3 was added after 5 min. The reaction mixture was stirred at room temperature overnight, then diluted with CH2Cl2 (40 mL). The organic phase was washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by preparative TLC (10% MeOH—CH2Cl2) afforded the title compound. MS (ESI): 511 (M+H)+.

Workup

  1. customTo a 20 mL flask equipped
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. washThe organic phase was washed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by preparative TLC (10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-0e9848536a0441fe8d6005e63e19f226
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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