Acetic Acid → HCID 68698324, compound

HRID 1990881Notes

Reaction equation

HRID 1990881 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[O:9][C:10]3[C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:3][CH2:2]1.[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH:26]=O)[CH3:21].[CH:33]([N:36](C(C)C)[CH2:37]C)(C)C.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.C(OCC)(=O)C.O>[CH3:33][N:36]([CH3:37])[C:17]([C:16]1[C:10]2[O:9][C:8]([NH:7][CH:4]3[CH2:3][CH2:2][N:1]([CH2:26][C:25]4[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:23]([O:22][CH2:20][CH3:21])[CH:24]=4)[CH2:6][CH2:5]3)=[N:12][C:11]=2[CH:13]=[CH:14][CH:15]=1)=[O:19]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68699762HCID 68699762, compound

Product 1

HCID 68698324HCID 68698324, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(piperidin-4-ylamino)-benzooxazole-7-carboxylic acid (0.35 g, 1.32 mmol, 1.0 equiv) and 3-ethoxy-4-methoxy-benzaldehyde (0.26 g, 1.45 mmol, 1.1 equiv) in ethanol (2 mL) was added diisopropylethylamine (0.39 mL, 0.43 g, 3.3 mmol, 2.5 equiv) and acetic acid (0.16 g, 2.64 mmol, 2.0 equiv) and the mixture stirred at 50° C. After 1.5 h sodium cyano borohydride (0.21 g, 3.3 mmol, 2.5 equiv) was added and the mixture stirred at 50° C. over night. The solvent was removed under reduced pressure and the crude reaction product dissolved in a mixture (1:1, 50 mL) of ethyl acetate and water adjusted to pH 7. The water phase was extracted two more times with ethyl acetate (2×50 mL), the combined organic phases dried over MgSO4 and the solvent evaporated to yield 0.55 g (99%) of the title compound which was used directly in the following step. MS (ISP): 426.0 [M+H]+.

Workup

  1. stirringthe mixture stirred at 50° C. over night
  2. customThe solvent was removed under reduced pressure
  3. customthe crude reaction product
  4. extractionThe water phase was extracted two more times with ethyl acetate (2×50 mL)
  5. dry with materialthe combined organic phases dried over MgSO4
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-62c4ad8d43a946248b26eb82dc7facb8
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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