Triethylamine → HCID 58997363, compound

HRID 1591878Notes

Reaction equation

HRID 1591878 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[N:10]=1.[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>O1CCOCC1.C(OCC)(=O)C.O>[NH2:15][C:11]1[N:10]=[C:9]([NH:8][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][C:17]([F:16])=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 88612,6-DiaminopyridineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 58997363HCID 58997363, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Combine triethylamine (15.8 mL, 111.0 mmol) and 2,6-diaminopyridine (6.5 g, 59.6 mmol) in dioxane (200 mL). Add 4-fluorobenzoyl chloride (5.46 mL, 44.7 mmol) in small increments. After complete addition, stir at room temperature for 18 hr. Pour into water and dilute with ethyl acetate and water. Separate and extract twice the aqueous layer with CH2Cl2, combine the organic fractions, dry over MgSO4, and concentrate. Chromatograph on silica gel, eluting with a gradient of 0%–10% (2M NH3 in methanol) in CH2Cl2 to give the title intermediate (8.91 g, 86.3%): mass spectrum (ion spray): m/z=232.3 (M+1); Analysis calc'd for C12H10N3OF.0.1H2O: C, 61.85; H, 4.41; N, 18.03. Found: C, 61.75; H, 4.08; N, 17.66.

Workup

  1. additionAfter complete addition
  2. customSeparate
  3. extractionextract twice the aqueous layer with CH2Cl2
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate
  6. washChromatograph on silica gel, eluting with a gradient of 0%–10% (2M NH3 in methanol) in CH2Cl2

Sources & evidence

ORD record
ord-56da5803f1984e83a1d96ab8e3a468f8
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Reaction notes

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