1,2-Dichloroethane → N-[2-(4-hydroxymethyl-phenyl)-ethyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide

HRID 1444720Notes

Reaction equation

HRID 1444720 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]1[CH2:18][C:19](O)=[O:20].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][OH:46])=[CH:41][CH:40]=1>C(Cl)Cl.CN(C=O)C>[OH:46][CH2:45][C:42]1[CH:43]=[CH:44][C:39]([CH2:38][CH2:37][NH:36][C:19](=[O:20])[CH2:18][CH:3]2[C:2](=[O:1])[NH:7][CH:6]=[CH:5][N:4]2[S:8]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)(=[O:9])=[O:10])=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 12671358[4-(2-Aminoethyl)phenyl]methanolHCID 686795602-(3-Oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid

Product 1

HCID 68678687N-[2-(4-hydroxymethyl-phenyl)-ethyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of [3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetic acid (620 mg, 2.0 mmol), EDC (Aldrich, 575 mg, 3.0 mmol), HOBt (Aldrich, 270 mg, 2.0 mmol), and [4-(2-amino-ethyl)-phenyl]-methanol (362 mg, 2.4 mmol) was added CH2Cl2 (15 mL) and DMF (2 mL). The reaction mixture was stirred at room temperature overnight and diluted with CH2Cl2 (80 mL). The organic phase was washed with saturated NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel chomatography (6%-10% MeOH—CH2Cl2) to afford the title compound. MS (ESI): 444 (M+H)+.

Workup

  1. washThe organic phase was washed with saturated NaHCO3, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by silica gel chomatography (6%-10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-95c682b01e4149138c1b502e0e4a8f25
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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