Triethylamine → HCID 67207417, compound

HRID 1799073Notes

Reaction equation

HRID 1799073 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][N:16]2[CH2:21][CH:20]3[CH2:22][CH:17]2[CH2:18][N:19]3C(=O)C)=[CH:13][CH:12]=1.CCN(CC)CC.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH3:35][S:36]([N:19]1[CH2:18][C@@H:17]2[CH2:22][C@H:20]1[CH2:21][N:16]2[CH2:15][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[CH:27][CH:26]=1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57670780HCID 57670780, compound

Product 1

HCID 67207417HCID 67207417, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5-(4-benzothiazol-2-ylmethyl-benzyl)-2,5-diaza-bicyclo[2.2.1]hept-2-yl]-ethanone (0.2 g, 0.49 mmol) in CH2Cl2 (5 mL) was added Et3N (0.41 mL, 3.0 mmol) and methanesulfonyl chloride (57 μL, 0.74 mmol) and the resulting solution was stirred at rt for 14 h. The reaction mixture was concentrated and the crude residue was partitioned between EtOAc (50 mL) and brine (50 mL). The organic layer was separated, dried (Mg2SO4), filtered and concentrated. Purification by silica gel flash chromatography (0% to 15% CH3OH in CH2Cl2) afforded the title compound as clear oil (0.13 g, 62%). MS (ESI): mass calcd. for C21H23N3O2S2, 413.56; m/z found, 414.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.01 (d, J=7.8 Hz, 1H), 7.81 (dd, J=7.8, 0.5 Hz, 1H), 7.49-7.45 (m, 1H), 7.37-7.34 (m, 5H), 4.44 (d, J=2.0 Hz, 2H), 4.31 (br s, 1H), 3.80 (d, J=13.8 Hz, 1H), 3.75 (d, J=13.8 Hz, 1H), 3.62-3.60 (m, 1H), 3.57 (br s, 1H), 3.24 (dd, J=9.3, 2.3 Hz, 1H), 2.90-2.89 (br m, 4H), 2.85-2.83 (br m, 1H), 1.96-1.94 (m, 1H), 1.74-1.72 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude residue was partitioned between EtOAc (50 mL) and brine (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel flash chromatography (0% to 15% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-6a33549c33324970a21787849917b593
Source dataset
uspto-grants-2013_01
Patent number
US08344008B2

Reaction notes

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