Triethylamine → 1-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl)azetidin-3-yl methanesulfonate

HRID 749440Notes

Reaction equation

HRID 749440 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:19][CH2:20][N:21]2[CH2:24][CH:23]([OH:25])[CH2:22]2)[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl>[CH3:41][S:42]([O:25][CH:23]1[CH2:24][N:21]([CH2:20][CH2:19][C@@H:18]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:17][N:15]([C:13]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:14])[CH3:16])[CH2:22]1)(=[O:44])=[O:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 689772843-cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide

Product 1

HCID 586835281-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl)azetidin-3-yl methanesulfonateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide (0.20 g, 0.41 mmol) was dissolved in CH2Cl2 and to the resultant solution was added triethylamine (0.17 mL, 0.41 mmol). The mixture was cooled to 0° C. before careful addition of methanesulfonyl chloride (0.03 mL, 0.41 mmol). The mixture was stirred with cooling for 30 min and then at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 and then washed with hydrochloric acid (1M), saturated NaHCO3 and then with brine. The organic solution was dried over MgSO4 and the solvent removed by evaporation. There was obtained 0.21 g (92%) of 1-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl]azetidin-3-yl methanesulfonate as a solid. LCMS: m/z 560 (M+)+.

Workup

  1. temperaturewith cooling for 30 min
  2. washwashed with hydrochloric acid (1M), saturated NaHCO3
  3. dry with materialThe organic solution was dried over MgSO4
  4. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-76a8e6a12702426abb51122c24dd523a
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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