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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 510542
Notes
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Reaction equation

HRID 510542 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent
3×

Procedure

(7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-ylmethanamine (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-ae858c0e14af4eec8c5f39057b229004
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096619B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes