Triethylamine → N-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}methanesulfonamide

HRID 17445Notes

Reaction equation

HRID 17445 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:5](=[C:7]([C:26]#[N:27])[C:8]([CH3:25])=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:10]=2[N:11]2[CH2:15][CH2:14][C@H:13]([N:16]([CH3:18])[CH3:17])[CH2:12]2)[N:6]=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37].[OH-].[Na+]>ClCCl.O>[C:26]([C:7]1[C:5]2[N:6]=[C:2]([NH:1][S:36]([CH3:35])(=[O:38])=[O:37])[O:3][C:4]=2[C:10]([N:11]2[CH2:15][CH2:14][C@H:13]([N:16]([CH3:17])[CH3:18])[CH2:12]2)=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]=1[CH3:25])#[N:27]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chloride2×HCID 529457382-Amino-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 68585254N-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}methanesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-Amino-7-[3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (#76) was suspended in dichloromethane (3.4 ml), then triethylamine (94.9 μl, 681 μmol) and methanesulfonyl chloride (52.7 μl, 681 μmol) were added with cooling with ice, then dichloromethane (10 ml) was added, followed by stirring with cooling with ice for 5 hours. Further, triethylamine (94.9 μl, 681 μmol) and methanesulfonyl chloride (52.7 μl, 681 μmol) were added with cooling with ice, followed by stirring at room temperature for 15 hours. Aqueous 1 N sodium hydroxide solution (5 ml) and water (5 ml) were added to the reaction liquid, and the aqueous layer was washed with diethyl ether (20 ml×2).

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice for 5 hours
  3. temperaturewith cooling with ice
  4. stirringby stirring at room temperature for 15 hours
  5. washthe aqueous layer was washed with diethyl ether (20 ml×2)

Sources & evidence

ORD record
ord-6eb859fe6f544a2ab6444c983e6c27be
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

Loading…