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

HRID 1444718

Reaction equation

HRID 1444718 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]([OH:21])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][CH2:45][OH:46])=[CH:39][CH:38]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[OH:46][CH2:45][CH2:44][CH2:43][C:40]1[CH:39]=[CH:38][C:37]([NH:36][C:19](=[O:21])[CH2:18][CH:3]2[C:2](=[O:1])[NH:7][CH:6]=[CH:5][N:4]2[S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:9])=[O:10])=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2204244-AminobenzenepropanolHCID 686795602-(3-Oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid

Product 1

HCID 68680705N-[4-(3-Hydroxy-propyl)-phenyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 20 mL vial was added [3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetic acid (500 mg, 1.61 mmol), EDC (Aldrich, 464 mg, 2.42 mmol), HOBt (Aldrich, 195 mg, 1.45 mmol), CH2Cl2 (5 mL), 3-(4-amino-phenyl)-propan-1-ol (731 mg, 4.84 mmol) and (iPr)2NEt (Aldrich, 0.56 mL, 3.22 mmol). The reaction mixture was stirred at room temperature overnight and diluted with CH2Cl2 (60 mL). The organic phase was washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel chomatography (6%-8% MeOH—CH2Cl2) to afford the title compound. MS (ESI): 444 (M+H)+.

Workup

  1. washThe organic phase was washed with saturated NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by silica gel chomatography (6%-8% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-b54f76736cfb4069b79c793d9202ff01
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Linked notes

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