Triethylamine → 1-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one

HRID 63840노트

반응식

HRID 63840 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([CH3:27])[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([CH3:26])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[NH:29]1[CH2:33][C:32](=[O:34])[NH:31][CH2:30]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C>ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([CH3:27])[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([N:29]4[CH2:33][C:32](=[O:34])[NH:31][CH2:30]4)=[O:22])=[C:19]([CH3:26])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 56965782Imidazolidin-4-one hydrochlorideHCID 1180469104-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid

생성물 1

HCID 1180467691-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid (100 mg, 0.25 mmol, 1.00 equiv) in dichloromethane (5 mL), imidazolidin-4-one hydrochloride (27.05 mg, 0.22 mmol, 1.00 equiv), HOBt (32.92 mg, 0.24 mmol, 1.10 equiv), triethylamine (33.59 mg, 0.33 mmol, 2.10 equiv), EDCI (63.85 mg, 0.33 mmol, 1.50 equiv). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 20 mL of water. The resulting solution was extracted with 3×10 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5-1:1). This resulted in 80 mg (68%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one as a white solid.

후처리

  1. customInto a 100-mL 3-necked round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 3×10 mL of dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThis resulted in 80 mg (68%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one as a white solid

출처 및 근거

ORD 기록
ord-b86362c907c34bbf832162fbeaeb0a9a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447084B2

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