Diisopropylethylamine → Ethyl 4-[(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)amino]butanoate

HRID 17567Notes

Reaction equation

HRID 17567 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(C(C)C)CC)(C)C.Cl[C:21]1[O:22][C:23]2[C:24](=[C:26]([C:38]#[N:39])[C:27]([CH3:37])=[C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:29]=2[F:30])[N:25]=1>ClCCl>[C:38]([C:26]1[C:24]2[N:25]=[C:21]([NH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[O:22][C:23]=2[C:29]([F:30])=[C:28]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:27]=1[CH3:37])#[N:39]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 51039317Ethyl 4-[(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)amino]butanoateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With cooling with ice, ethyl 4-aminobutanoate hydrochloride (149 mg, 0.892 mmol) and diisopropylethylamine (303 μl, 1.78 mmol) were added to a dichloromethane (7 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (213 mg, 0.743 mmol), followed by stirring at room temperature for 15 hours. The reaction liquid was concentrated under reduced pressure, ethyl acetate was added, followed by washing with saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1→1:1, v/v) to obtain the entitled compound (279 mg, 99%) as a white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure, ethyl acetate
  3. additionwas added
  4. washby washing with saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe insoluble matter was separated by filtration
  7. customthe residue obtained by concentration
  8. customwas purified by silica gel column chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-fb2454710843437e9f5796ddf51d79d1
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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