1-methyl-1H-imidazole-4-sulfonyl chloride → N-{[7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl]methyl}-1-methyl-1H-imidazole-4-sulfonamide

HRID 1044525Notes

Reaction equation

HRID 1044525 reaction equation
[N:1]1([CH:5]2[CH:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]3[CH:12]=[C:11]([CH2:22][NH2:23])[CH:10]=[CH:9][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[CH3:24][N:25]1[CH:29]=[C:28]([S:30](Cl)(=[O:32])=[O:31])[N:27]=[CH:26]1>CN(C1C=CN=CC=1)C.ClCCl>[N:1]1([CH:5]2[CH:14]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:13]3[CH:12]=[C:11]([CH2:22][NH:23][S:30]([C:28]4[N:27]=[CH:26][N:25]([CH3:24])[CH:29]=4)(=[O:32])=[O:31])[CH:10]=[CH:9][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 595477987-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-ylmethanamine

Product 1

HCID 57471402N-{[7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl]methyl}-1-methyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

(7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanamine (250 mg, 0.816 mmol) and N,N-dimethyl-4-aminopyridine (199 mg, 1.632 mmol) were dissolved in dichloromethane (18 mL). 1-Methyl-1H-imidazole-4-sulfonyl chloride (147 mg, 0.816 mmol) dissolved in dichloromethane (2 mL) was added dropwise. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with dichloromethane (20 mL) and washed successively with saturated ammonium chloride (3×15 mL) and water (2×10 mL). The organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 64 mg (0.142 mmol, 17%).

Workup

  1. additionwas added dropwise
  2. washwashed successively with saturated ammonium chloride (3×15 mL) and water (2×10 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent was evaporated in vacuo
  5. customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record
ord-178e6bc87c914ad7b0e7639ad38eede1
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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