Water → HCID 76739682, compound

HRID 2189052Notes

Reaction equation

HRID 2189052 reaction equation
ClC1N=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=CC=2)[CH:5]=[C:4]2[O:14][CH:15]=[CH:16][C:3]=12.[C:17]([O:21][C:22](=[O:32])[CH2:23][O:24][C@H:25]1[CH2:30][CH2:29][CH2:28][C@H:27]([NH2:31])[CH2:26]1)([CH3:20])([CH3:19])[CH3:18].[CH:33]([N:36]([CH2:40]C)C(C)C)(C)C.O.C[N:44](C=O)C>>[C:17]([O:21][C:22](=[O:32])[CH2:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([NH:31][C:33]2[C:16]3[CH:3]=[C:4]([C:5]4[CH:6]=[CH:8][CH:13]=[CH:12][CH:11]=4)[O:14][C:15]=3[N:44]=[CH:40][N:36]=2)[CH2:26]1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 58280166HCID 58280166, compoundHCID 86653756HCID 86653756, compound

Product 1

HCID 76739682HCID 76739682, compound

Conditions

Temperature
120 °C

Procedure

Initially charge 1.61 g (6.98 mmol) of 4-chloro-6-phenylfuro[2,3-d]pyridine and 1.60 g (6.98 mmol) of (+/−)-trans-{[3-aminocyclohexyl]oxy}acetic acid tert-butyl ester in 6.0 ml of DMF and add 1.8 ml (10.5 mmol) of N,N-diisopropylethylamine. Heat the reaction mixture to 120° C. for 3 h, then cool to RT and add to water. Extract three times with ethyl acetate, combine the organic phases, wash with satd. sodium chloride solution and concentrate under reduced pressure. From the residue, after purification by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 20:1→2:1), 1.67 g of the target product are isolated (56.5% of theory).

Workup

  1. temperaturecool to RT
  2. extractionExtract three times with ethyl acetate
  3. washwash with satd
  4. concentrationsodium chloride solution and concentrate under reduced pressure
  5. customFrom the residue, after purification by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 20:1→2:1), 1.67 g of the target product
  6. customare isolated (56.5% of theory)

Sources & evidence

ORD record
ord-13fa5af7420a4a2c9ccb45934a023ad4
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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