4-Methylmorpholine → Benzyl (7-(trifluoromethyl)isoquinolin-1-yl)carbamate

HRID 2175568Notes

Reaction equation

HRID 2175568 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[C:10]2[NH2:13])=[CH:5][CH:4]=1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].CN1CCOCC1>C(Cl)Cl>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[C:10]2[NH:13][C:17](=[O:18])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10387Benzyl chloroformateHCID 585625367-(Trifluoromethyl)isoquinolin-1-amine

Product 1

HCID 58562812Benzyl (7-(trifluoromethyl)isoquinolin-1-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-(trifluoromethyl)isoquinolin-1-amine (410 mg, 1.9 mmol), from above step E, and benzyl chloroformate (0.33 mL, 2.3 mmol) in DCM was treated with N-methylmorpholine (0.23 mL, 2.1 mmol) and stirred at room temperature for 18 h. Reaction mixture was diluted with DCM and washed with water and dried over Na2SO4. DCM was removed under vacuum and the residue was purified by silica column chromatography to give the title compound.

Workup

  1. customReaction mixture
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customDCM was removed under vacuum
  5. customthe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-c0cdbc0ea8054ff7ae48dee2bf1775bf
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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