Diisopropylethylamine → HCID 58503946, compound

HRID 2407791Notes

Reaction equation

HRID 2407791 reaction equation
Cl.[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]([C:19]([O:21][CH3:22])=[O:20])=[C:4]1[CH2:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.[C:30]1([C:36]2[CH:40]=[C:39]([CH:41]=O)[O:38][N:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(C(C)C)CC)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C>[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]([C:19]([O:21][CH3:22])=[O:20])=[C:4]1[CH2:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:41][C:39]2[O:38][N:37]=[C:36]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:40]=2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 113672673-Phenyl-1,2-oxazole-5-carbaldehydeHCID 66989627HCID 66989627, compound

Product 1

HCID 58503946HCID 58503946, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in Example 306 (83.0 mg) and the compound prepared in Example 7 (52.2 mg) in dichloromethane (5.0 mL) was added diisopropylethylamine (0.105 mL) and sodium triacetoxyborohydride (85.2 mg). The reaction mixture was stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate, washed with saturated aqueous solution of sodium hydrogen carbonate, brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=9:1) to obtain the title compound (72.0 mg) having the following physical data.

Workup

  1. washwashed with saturated aqueous solution of sodium hydrogen carbonate, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=9:1)

Sources & evidence

ORD record
ord-f7092aa3d2354416937fadd4f8a63a09
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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