Chloroform → HCID 10616642, compound

HRID 1970795Notes

Reaction equation

HRID 1970795 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:4][N:3]=1.C(Cl)(Cl)Cl.[C:27](Cl)(=[O:29])[CH3:28].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:27]([NH:1][C:2]1[C:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:5]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[CH:4][N:3]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 113007862-Amino-3-benzyl-5-(4-methoxyphenyl)pyrazine

Product 1

HCID 10616642HCID 10616642, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under an argon atmosphere, 2-amino-3-benzyl-5-(4-methoxyphenyl)pyrazine (c-11) (prepared by the method described in Adamczyk, M. et al., Org. Prep. Proced. Int., 33, 477-485 (2001)) (199 mg, 681 μmol) was dissolved in anhydrous pyridine (1.4 mL) and chloroform (4 mL) and cooled to 0° C. To this was added acetyl chloride (365 μL, 5.13 mmol) and stirred for an hour after warming to room temperature. To this was added saturated aqueous solution of sodium bicarbonate to stop the reaction, and extracted 3 times with dichloromethane. The organic layer was washed with saturated aqueous solution of sodium sulfate and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated under reduced pressure with a rotary evaporator. The residue was recrystallized from methanol to give 2-acetylamino-3-benzyl-5-(4-methoxyphenyl)pyrazine (c-24) as a colorless solid (74.6 mg, 32.9%). Rf=0.14 (n-hexane/ethyl acetate=3/2). UV (MeOH) λmax (log ε) 329.5 (4.18), 293 (4.18), 274 (4.16). UV (pH 7.4 PB) λmax (log ε) 328 (4.11), 289.5 (4.01), 270.5 (4.05). 1H NMR (400 MHz, DMSO-d6) δ 2.04 (s, 3H), 3.81 (s, 3H), 4.15 (s, 2H), 7.02-7.08 (AA′BB′, 2H), 7.15-7.22 (m, 3H), 7.23-7.29 (m, 2H), 8.00-8.05 (AA′BB′, 2H), 8.87 (s, 1H), 10.25 (s, 1H). IR (KBr, cm−1) 698, 744, 833, 1032, 1157, 1175, 1213, 1256, 1285, 1327, 1368, 1416, 1450, 1499, 1543, 1587, 1609, 1670, 3258. HRMS (FAB+) m/z 334.1557 (M+H, C20H20N3O2 requires 334.1556).

Workup

  1. customthe reaction
  2. extractionextracted 3 times with dichloromethane
  3. washThe organic layer was washed with saturated aqueous solution of sodium sulfate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing anhydrous sodium sulfate
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated under reduced pressure with a rotary evaporator
  8. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-e2d58efdb61247718110634bb832df47
Source dataset
uspto-grants-2013_04
Patent number
US08431525B2

Reaction notes

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