Triethylamine → HCID 178478363, compound

HRID 707288Notes

Reaction equation

HRID 707288 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:14][C@@H:13]([NH2:15])[CH2:12]1.[Cl:16][C:17]1[C:22](Cl)=[N:21][CH:20]=[CH:19][N:18]=1.C(N(CC)CC)C>CS(C)=O.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:12][C@@H:13]([NH:15][C:22]2[C:17]([Cl:16])=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:14]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 785752,3-DichloropyrazineHCID 178511737HCID 178511737, compound

Product 1

HCID 178478363HCID 178478363, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a round bottomed flask was added cis-N1-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine (0.5306 g, 1.816 mmol), 2,3-dichloropyrazine (0.271 g, 1.816 mmol, Pfaltz & Bauer, Inc.), and triethylamine (0.758 ml, 5.45 mmol, Sigma-Aldrich Chemical Company, Inc.) to stir at 75° C. in DMSO (1.816 ml) to stir for 6 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic extract was washed with water, saturated NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (50 g), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide the title compound (0.1952 g, 0.588 mmol, 32.4% yield). LCMS showed product peak at 1.625 min (m+1=332.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.06-2.20 (m, 2 H) 2.75-2.87 (m, 2 H) 3.98-4.11 (m, 1 H) 4.11-4.22 (m, 1 H) 7.03 (td, J=7.53, 1.17 Hz, 1 H) 7.19-7.28 (m, 2 H) 7.40 (d, J=7.24 Hz, 1 H) 7.60 (d, J=2.54 Hz, 1 H) 7.69 (dd, J=7.82, 0.78 Hz, 1 H) 8.05 (d, J=2.74 Hz, 1 H) 8.32 (d, J=6.65 Hz, 1 H)

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe organic extract
  3. washwas washed with water, saturated NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed through a Biotage SNAP HP-silica gel column (50 g)
  8. washeluting with a gradient of 10% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-d95635cb1b7d4f6ebb86e17f6a9d8393
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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