Acetonitrile → (S)-2-amino-3-(4-(5-(naphthalen-2-ylmethylamino)pyrazin-2-yl)phenyl)propanoic acid

HRID 469874Notes

Reaction equation

HRID 469874 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[N:6][CH:7]=1.[C:20]([O-:23])([O-])=[O:21].[Na+].[Na+].[C:26](#[N:28])[CH3:27]>[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2].O>[NH2:28][C@@H:26]([CH2:27][C:10]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[N:6][C:5]([NH:8][CH2:9][C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:11]=3)=[CH:4][N:3]=2)=[CH:12][CH:11]=1)[C:20]([OH:23])=[O:21]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 866143075-bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amine

Product 1

HCID 24894502(S)-2-amino-3-(4-(5-(naphthalen-2-ylmethylamino)pyrazin-2-yl)phenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 22065850Palladium(2+);triphenylphosphane;dichlorideCatalystHCID 962WaterSolvent

Procedure

5-Bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amine (0.2 g, 0.637 mmol), L-p-boronophenylalanine (0.13 g, 0.637 mmol), palladiumtriphenylphosphine dichloride (13 mg, 0.019 mmol), Na2CO3 (0.13 g, 1.27 mmol), acetonitrile (5 mls) and water (5 mls) were heated in a microwave reactor at 150° C. for 5 minutes. The mixture was concentrated, dissolved in 1.0 N HCl, washed twice with ether, concentrated, dissolved in methanol, filtered and concentrated to yield 0.12 g of the captioned compound. M+1=399; 1H NMR (CD3OD) δ 8.51 (s, 1H), 8.37 (s, 1H), 7.90 (m, 6H), 7.50 (m, 5H), 4.85 (s, 2H), 4.30 (t, 1H), 3.38 (m, 1H), 3.22 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in 1.0 N HCl
  3. washwashed twice with ether
  4. concentrationconcentrated
  5. dissolutiondissolved in methanol
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-584bab270fe34a04bc04bf797b41e6a8
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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