Sodium hydride → Methyl 2-(((benzyloxy)carbonyl)(7-(trifluoromethyl)isoquinolin-1-yl)amino)acetate

HRID 1896887Notes

Reaction equation

HRID 1896887 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[C:10]2[NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CN(C=O)C>[CH2:16]([O:15][C:14]([N:13]([C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([C:2]([F:24])([F:1])[F:25])[CH:12]=2)[CH:7]=[CH:8][N:9]=1)[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 58562812Benzyl (7-(trifluoromethyl)isoquinolin-1-yl)carbamate

Product 1

HCID 58562656Methyl 2-(((benzyloxy)carbonyl)(7-(trifluoromethyl)isoquinolin-1-yl)amino)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzyl (7-(trifluoromethyl)isoquinolin-1-yl)carbamate (212 mg, 0.61 mmol), from above step F in DMF (5 mL) was cooled in an ice bath and treated with NaH (27 mg, 0.67 mmol), and the mixture was stirred for 30 min and was treated with methyl bromoacetate (64 μL, 0.67 mmol). This solution was stirred and allowed to warm to room temperature over 18 h. The reaction was quenched with saturated NH4Cl and DMF was removed under vacuum. The residue was taken in EtOAc and washed with water, sat NaCl and dried over Na2SO4. EtOAc was removed under vacuum and the residue was purified by silica column chromatography to give the title compound.

Workup

  1. stirringThis solution was stirred
  2. customThe reaction was quenched with saturated NH4Cl and DMF
  3. customwas removed under vacuum
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customEtOAc was removed under vacuum
  7. customthe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-3253b1db77df463691f46cf00eed1bea
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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