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Triethylamine → 3-(2-methoxy-4-{2-(4-trifluoromethyl-phenyl)-4-[(3,3,3-trifluoro-propylamino)-methyl]-thiazol-5-ylmethoxy}-phenyl)-4H-[1,2,4]oxadiazol-5-one

HRID 2263412
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HRID 2263412 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[C:28]1[NH:32][C:31](=[O:33])[O:30][N:29]=1)[O:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH:23]=O.C(N(CC)CC)C.Cl.[F:42][C:43]([F:48])([F:47])[CH2:44][CH2:45][NH2:46].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:6][CH2:7][C:8]2[S:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][CH:14]=3)=[N:10][C:9]=2[CH2:23][NH:46][CH2:45][CH2:44][C:43]([F:48])([F:47])[F:42])[CH:25]=[CH:26][C:27]=1[C:28]1[NH:32][C:31](=[O:33])[O:30][N:29]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 252105053,3,3-Trifluoropropylamine hydrochlorideHCID 136149986HCID 136149986, 화합물

생성물 1

HCID 1361499463-(2-methoxy-4-{2-(4-trifluoromethyl-phenyl)-4-[(3,3,3-trifluoro-propylamino)-methyl]-thiazol-5-ylmethoxy}-phenyl)-4H-[1,2,4]oxadiazol-5-one수율 18%

시약·촉매·용매

1
HCID 887Methanol용매

실험 절차

To a suspension of 30 mg of 5-[3-methoxy-4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazole-4-carbaldehyde in 1.5 mL of methanol were added 0.018 mL of triethylamine, 10 mg of 3,3,3-trifluoro-propylamine hydrochloride and 0.5 g of 4 Å powdered molecular sieves. The resulting mixture was stirred at room temperature for 1 h then 2.4 mg of sodium borohydride was added. After stirring at room temperature for 45 minutes, the reaction mixture was concentrated under reduced pressure. The crude product was purified by preparative thin layer chromatography on silica gel (dichloromethane 90/methanol 10/water 1/acetic acid 1) followed by azeotropal removal of traces of acetic acid with cyclohexane to give 6.5 mg of 3-(2-methoxy-4-{2-(4-trifluoromethyl-phenyl)-4-[(3,3,3-trifluoro-propylamino)-methyl]-thiazol-5-ylmethoxy}-phenyl)-4H-[1,2,4]oxadiazol-5-one as a white solid.

후처리

  1. stirringAfter stirring at room temperature for 45 minutes
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe crude product was purified by preparative thin layer chromatography on silica gel (dichloromethane 90/methanol 10/water 1/acetic acid 1)
  4. customfollowed by azeotropal removal of traces of acetic acid with cyclohexane

출처 및 근거

ORD 기록
ord-c774b45ead2841a9b0c84ef51fdbebc6
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07851493B2

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