1-Isoquinolinamine → HCID 70925802, compound

HRID 1502595Notes

Reaction equation

HRID 1502595 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:12][C:13]1[S:14][C:15]([CH2:18]Cl)=[CH:16][N:17]=1>CN1CCCC1=O.O>[Cl:12][C:13]1[S:14][C:15]([CH2:18][NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:16][N:17]=1

Participants

5

Reactant 2

HCID 737421-IsoquinolinamineHCID 27631792-Chloro-5-chloromethylthiazole

Product 1

HCID 70925802HCID 70925802, compoundYield 10.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 1-aminoisoquinoline (0.56 g, 3.9 mmol) and 2-chloro-5-(chloromethyl)thiazole (0.50 g, 3.0 mmol) in N-methylpyrrolidinone (3 mL) was heated to 220° C. in a microwave reactor for 10 min. The reaction mixture was cooled to room temperature, diluted with water (20 mL), and extracted with diethyl ether (5×20 mL). The combined organic extracts were concentrated under reduced pressure, and the resulting residue was purified by chromatography on silica gel eluted with 20-50% ethyl acetate/hexane to give the title compound as a pale yellow solid (0.09 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with diethyl ether (5×20 mL)
  3. concentrationThe combined organic extracts were concentrated under reduced pressure
  4. customthe resulting residue was purified by chromatography on silica gel
  5. washeluted with 20-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ceb67c09088147a995e284fcbcde4e33
Source dataset
uspto-grants-2015_12
Patent number
US09210932B2

Reaction notes

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