Triethylamine → HCID 71811361, compound

HRID 714063Notes

Reaction equation

HRID 714063 reaction equation
[NH2:1][CH:2]1[C:11]2[CH:10]=[N:9][CH:8]=[C:7]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21].CCN(CC)CC>C(Cl)Cl>[C:16]([C:15]1[CH:14]=[CH:13][C:12]([C:7]2[C:6]3[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[C:11]=3[CH:10]=[N:9][CH:8]=2)=[CH:19][CH:18]=1)#[N:17]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 11667Ethanesulfonyl chloride2×HCID 718113604-(8-Amino-5,6,7,8-tetrahydro-4-isoquinolinyl)benzonitrile

Product 1

HCID 71811361HCID 71811361, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of (rac)-4-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile (example 1) (62.3 mg, 250 μmol) in CH2Cl2 (3.6 ml) was treated with ethanesulfonyl chloride (26.6 μL, 275 μmol) and Et3N (41.8 μL, 300 μmol). After ½ h the mixture was stirred at room temperature for 3 h, cooled down (0° C.) and treated again with ethanesulfonyl chloride (7.3 μL, 75 μmol) and Et3N (11.5 μL, 82.5 μmol). After 2 h at room temperature, the mixture was concentrated in vacuo and purified by flash chromatography (20 g SiO2, Telos-cartridge, CH2Cl2/MeOH (0.5 to 1.5%)) to give after precipitation from CH2Cl2 with n-pentane the pure title compound (43 mg, 50%) as a off-white powder. MS: 342.1 (M+H+).

Workup

  1. temperaturecooled down (0° C.)
  2. waitAfter 2 h at room temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. custompurified by flash chromatography (20 g SiO2, Telos-cartridge, CH2Cl2/MeOH (0.5 to 1.5%))
  5. customto give
  6. customafter precipitation from CH2Cl2 with n-pentane the pure title compound (43 mg, 50%) as a off-white powder

Sources & evidence

ORD record
ord-879154df2bb34e79b3a827d05528a835
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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