Tetrahydrofuran → HCID 22668924, compound

HRID 1007228Notes

Reaction equation

HRID 1007228 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[N:16][CH:15]=[CH:14][N:13]=1.C1COCC1.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:11][C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)=[O:7])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 78747AminopyrazineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 22668924HCID 22668924, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 6-chloronicotinoyl chloride (160 mg, 0.91 mmol), aminopyrazine (87 mg, 0.91 mmol) and THF (10 ml) was added triethylamine (0.25 ml, 1.82 mmol) and the mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate (100 ml), wash with water (50 ml), saturated aqueous NaCl (50 ml), dried over anhydrous sodium sulfate and evaporated. The crude product was purified by column chromatography using hexane:ethyl acetate (3:2) to give 8 mg (4% yield) of the title compound as yellow solid. 1H NMR (CDCl3): 9.68 (d, J=1.2 Hz, 1H), 8.95 (d, J=2.7 Hz, 1H), 8.45 (d, J=2.7 Hz, 1H), 8.4 (bs, 1H), 8.33-8.32 (m, 1H), 8.23 (dd, J=2.4, 8.1 Hz, 1H), 7.53 (dd, J=0.6, 8.4 Hz, 1H).

Workup

  1. washwash with water (50 ml), saturated aqueous NaCl (50 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a08dc8bde2f247b5bae8473ee8bca6be
Source dataset
uspto-grants-2004_09
Patent number
US06794397B2

Reaction notes

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