Triethylamine → 5-Cyclohexyl-2-methyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide

HRID 2236311Notes

Reaction equation

HRID 2236311 reaction equation
[CH:1]1([C:7]2[O:11][C:10]([CH3:12])=[C:9]([C:13]([OH:15])=O)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:16]1([C:22]2[N:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[N:16]1([C:22]2[N:27]=[CH:26][C:25]([NH:28][C:13]([C:9]3[CH:8]=[C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[O:11][C:10]=3[CH3:12])=[O:15])=[CH:24][CH:23]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1040596-(Morpholino)pyridin-3-amineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 593014193-Furancarboxylic acid, 5-cyclohexyl-2-methyl-

Product 1

HCID 593012875-Cyclohexyl-2-methyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amideYield 64.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Cyclohexyl-2-methyl-furan-3-carboxylic acid (83 mg, 0.365 mmol), 6-morpholin-4-yl-pyridin-3-ylamine (83 mg, 0.4 mmol), and triethylamine (154 uL, 1.09 mmol) were dissolved in 5 mL of DMF and chilled in an ice bath. To this solution was added BOP (169 mg, 0.383 mmol) in one portion. The mixture was stirred at room temperature for one hour and then diluted with 30 mL ethyl acetate. The ethyl acetate solution was washed with saturated sodium bicarbonate (2×10 mL) and saturated sodium chloride (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to dryness under vacuum. The crude product was purified by flash chromatography using ethyl acetate/hexane to yield 5-cyclohexyl-2-methyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide as a light grey powder (87 mg, 64%). ES-MS calcd for C21H27N3O3 (m/e) 369.5, obsd 370.3 (M+H).

Workup

  1. temperaturechilled in an ice bath
  2. washThe ethyl acetate solution was washed with saturated sodium bicarbonate (2×10 mL) and saturated sodium chloride (10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness under vacuum
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ed832a36ad824a7786b6cdbfd719c1bf
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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