461-28-9 → HCID 59547781, compound

HRID 2177075Notes

Reaction equation

HRID 2177075 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][NH2:19])=[CH:13][CH:14]=2)[CH:9]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:4])([CH3:3])[CH3:2].[F:28][CH2:29][CH2:30][CH2:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][NH:19][S:32]([CH2:31][CH2:30][CH2:29][F:28])(=[O:34])=[O:33])=[CH:13][CH:14]=2)[CH:9]1[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21114841461-28-9HCID 57471193Tert-butyl [7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

Product 1

HCID 59547781HCID 59547781, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl[7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate (32 mg, 0.87 mmol) was dissolved in dichloromethane (15 mL) and 4-dimethylaminopyridine (12 mg, 0.096 mmol) and 3-fluoropropane-1-sulfonyl chloride (14 mg, 0.087 mmol) were added. The reaction mixture was stirred at room temperature over night. The dichloromethane solution of the crude product was washed successively with 1N aqueous hydrochloric acid and aqueous NaHCO3 solution, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane, methanol, silica gel). Yield: 9.3 mg (0.019 mmol, 22%).

Workup

  1. washThe dichloromethane solution of the crude product was washed successively with 1N aqueous hydrochloric acid and aqueous NaHCO3 solution
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (dichloromethane, methanol, silica gel)

Sources & evidence

ORD record
ord-d1bd3a3ef1f84c7f9919decb70bbfc0e
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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