Methanol → HCID 71811365, compound

HRID 714067Notes

Reaction equation

HRID 714067 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.[C:20](Cl)(=[O:22])[CH3:21].CCN(CC)CC.CO>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][C:20](=[O:22])[CH3:21])[C:11]=3[CH:10]=[N:9][CH:8]=2)=[CH:19][CH:18]=1)#[N:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 718113604-(8-Amino-5,6,7,8-tetrahydro-4-isoquinolinyl)benzonitrile

Product 1

HCID 71811365HCID 71811365, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (−20° 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 acetyl chloride (21.3 μL, 275 μmol) and Et3N (41.8 μL, 300 μmol). After ½ h, an additional drop of acetyl chloride was added and after 5 min. the mixture was treated with MeOH (0.2 mL) and extracted with water/AcOEt (3×). The organic phases were dried over Na2SO4, filtered and evaporated under reduced pressure. Purification by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (2 to 3%)) and precipitation from CH2Cl2 with n-pentane gave the title compound (32 mg, 44%) as off-white powder. MS: 292.1 (M+H+).

Workup

  1. extractionextracted with water/AcOEt (3×)
  2. dry with materialThe organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customPurification
  6. customby flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (2 to 3%)) and precipitation from CH2Cl2 with n-pentane

Sources & evidence

ORD record
ord-b3f37c8c20a84311889dc85bf9c358c3
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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