Water → HCID 66868885, compound

HRID 242044Notes

Reaction equation

HRID 242044 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25]C(=O)OC(C)(C)C)[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.NC1C=CC=CN=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42].O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:41]([CH3:40])(=[O:43])=[O:42])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 104392-AminopyridineHCID 31297Methanesulfonyl chlorideHCID 66868974HCID 66868974, compound

Product 1

HCID 66868885HCID 66868885, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1-(1-(4-chlorophenyl)cyclobutyl)-3,4-dihydroisoquinolin-7-yloxy)ethanamine (example 1, 100 mg, 0.26 mmol), aminopyridine (34.0 mg, 0.28 mmol), and methanesulfonyl chloride (31.9 mg, 0.28 mmol) were dissolved in THF (5 ml) and stirred for 14 h at RT. Water was added and the mixture was extracted with ethyl acetate. The organic layers were washed with water and saturated NaCl solution, dried with MgSO4, and the solvent was removed. The residue was purified by flash chromatography on silica gel using methylenehloride/MeOH 98:2→95:5 to give N-(2-{1-[1-(4-Chloro-phenyl)-cyclobutyl]-3,4-dihydro-isoquinolin-7-yloxy}-ethyl)-methanesulfonamide (90.0 mg, 0.21 mmol, 78%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layers were washed with water and saturated NaCl solution
  3. dry with materialdried with MgSO4
  4. customthe solvent was removed
  5. customThe residue was purified by flash chromatography on silica gel using methylenehloride/MeOH 98:2→95:5

Sources & evidence

ORD record
ord-6a1048760efc459f9a34784c4379ed37
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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