Water → HCID 86646903, compound

HRID 1044510Notes

Reaction equation

HRID 1044510 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:10]=[C:9]([O:20][CH2:21][CH2:22][N:23]([CH3:33])[S:24]([C:27]3[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=3)(=[O:26])=[O:25])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]1.Br[CH2:35][CH2:36][CH2:37][CH2:38]Br.C(N(CC)CC)C.O>C(#N)C.C(OCC)(=O)C>[ClH:1].[CH2:13]([CH:12]1[C:11]2[CH:10]=[C:9]([O:20][CH2:21][CH2:22][N:23]([CH3:33])[S:24]([C:27]3[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=3)(=[O:26])=[O:25])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH:3]1[N:2]1[CH2:38][CH2:37][CH2:36][CH2:35]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 8471TriethylamineHCID 86646904HCID 86646904, compound

Product 1

HCID 86646903HCID 86646903, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

N-(2-{[7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-N,1-dimethyl-1H-imidazole-4-sulfonamide hydrochloride (98), 1,4-dibromobutane (49.9 mg, 0.231 mmol), and triethylamine (31.2 mg, 0.308 mmol) were dissolved in acetonitrile (3 ml) and stirred for 2 h at 130° C. in the microwave. Water and ethyl acetate were added and the organic phase was separated. After extraction of the aqueous phase with ethylacetate the combined organic layers were washed with saturated NaCl solution, dried over Na2SO4, and concentrated to afford a residue a residue that was purified by flash chromatography (silica gel, MeOH/CH2Cl2 5:95). The residue was transferred to an HCl salt and finally gave the product as a white solid (8.5 mg, 10%) after precipitation from diisopropylether.

Workup

  1. customthe organic phase was separated
  2. extractionAfter extraction of the aqueous phase with ethylacetate the combined organic layers
  3. washwere washed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford a residue a residue that
  7. customwas purified by flash chromatography (silica gel, MeOH/CH2Cl2 5:95)

Sources & evidence

ORD record
ord-df776ae9c7a74ff6b0b2762ce4b5b9d3
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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