Acetyl chloride → HCID 57471362, compound

HRID 1044519Notes

Reaction equation

HRID 1044519 reaction equation
[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[C:10]2[CH:9]=[C:8]([CH2:20][CH2:21][CH2:22][NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>ClCCl>[F:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:20][CH2:21][CH2:22][NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[CH:9]=2)[CH2:4][CH2:3][CH:2]1[NH:1][C:37](=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57471353HCID 57471353, compound

Product 1

HCID 57471362HCID 57471362, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(3-(7-Amino-8-(3-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl)propyl)propane-1-sulfonamide (cf. example 209: 45 mg, 0.108 mmol) and triethylamine (15 μL, 0.108 mmol) were dissolved in dichloromethane (2 mL). Acetylchloride (7.64 μL, 0.108 mmol) were added. The reaction mixture was stirred for 12 hours at room temperature. The reaction mixture was diluted with dichloromethane and successively washed with hydrochloric acid, water and saturated sodium chloride solution. The organic layer was dried and concentrated in vacuo. The crude product was purified by flash-chromatography (silica gel, dichloromethane, methanol). Yield: 37 mg (0.08 mmol, 75%).

Workup

  1. washsuccessively washed with hydrochloric acid, water and saturated sodium chloride solution
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash-chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record
ord-8e5fe96c8c154211950dafd689c318a0
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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