Triethylamine → HCID 58997363, compound

HRID 1716901Notes

Reaction equation

HRID 1716901 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 calculated 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-f7b39bfc5f5c47ab9ed31b478d97167b
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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