Triethylamine → tert-Butyl 6-(6-bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1918839Notes

Reaction equation

HRID 1918839 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]2.Br[C:20]1[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=[C:24]([Br:26])[N:25]=1.C(N(CC)CC)C>CC(O)C>[Br:26][C:24]1[N:25]=[C:20]([NH:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]3)[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27563716-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinolineHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

Product 1

HCID 58044031tert-Butyl 6-(6-bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (3 g, 12 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (2.68 g, 10 mmol), and triethylamine (1.5 g, 15 mmol) in IPA (50 mL) was heated at 70° C. for 15 h. The mixture was cooled to room temperature. The resulting yellow solids were collected by filtration and dried in vacuum to afford 120a as a yellow solid (2.83 g, 65%).MS: [M+H]+ 435.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe resulting yellow solids were collected by filtration
  3. customdried in vacuum

Sources & evidence

ORD record
ord-976427a892224973af022a3b5ef70c5d
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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