Tert-Butylamine → Methyl 1-(t-butylamino)isoquinoline-5-carboxylate

HRID 1051241Notes

Reaction equation

HRID 1051241 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N+:9]([O-])=[CH:10]2)=[O:4].FC(F)(F)C1C=CC=CC=1.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27].C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>C(OCC)(=O)C>[C:26]([NH:30][C:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]=2[CH:7]=[CH:8][N:9]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 7368(Trifluoromethyl)benzeneHCID 77773Toluene-p-sulphonic anhydrideHCID 1180908815-(Methoxycarbonyl)isoquinoline 2-oxide

Product 1

HCID 118090799Methyl 1-(t-butylamino)isoquinoline-5-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(Methoxycarbonyl)isoquinoline 2-oxide (2.0 g, 9.84 mmol) obtained in Step (4) above and trifluorotoluene (20 mL) were mixed and stirred. The reaction solution was slowly added with t-butylamine (3.6 g, 49.25 mmol) and p-toluenesulfonic acid anhydride (6.42 g, 19.68 mmol) at about 5° C., and stirred for about 2 hours at the same temperature (˜5° C.). The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.6 g, 64%).

Workup

  1. stirringstirred for about 2 hours at the same temperature (˜5° C.)
  2. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0fa38569ac8348a19b72e6096faae692
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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