Diisopropylethylamine → HCID 44253162, 화합물

HRID 2388675노트

반응식

HRID 2388675 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:16][CH2:17][O:18][CH2:19][C:20](O)=[O:21])[CH:13]1[CH2:15][CH2:14]1)(=[O:11])=[O:10].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[N:58]1([CH2:62][C:63]2[S:71][C:70]3[CH2:69][CH2:68][NH:67][CH2:66][C:65]=3[CH:64]=2)[CH2:61][CH2:60][CH2:59]1.C(N(C(C)C)C(C)C)C>O1CCCC1>[N:58]1([CH2:62][C:63]2[S:71][C:70]3[CH2:69][CH2:68][N:67]([C:20](=[O:21])[CH2:19][O:18][CH2:17][CH2:16][N:12]([CH:13]4[CH2:14][CH2:15]4)[S:9]([C:3]4[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])(=[O:11])=[O:10])[CH2:66][C:65]=3[CH:64]=2)[CH2:61][CH2:60][CH2:59]1

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 57916235HCID 57916235, 화합물HCID 68644042HCID 68644042, 화합물

생성물 1

HCID 44253162HCID 44253162, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-(2-(2-Chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetic acid (AC27) (100 mg, 0.288 mmol), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyl-uronium tetrafluoroborate (92 mg, 0.288 mmol) and 1-hydroxybenzotriazole hydrate (40 mg, 0.288 mmol) were dissolved in tetrahydrofuran (3.5 ml) and the mixture was stirred at room temperature for 30 min. A solution of 2-(azetidin-1-ylmethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine dihydrochloride (TP13) (97 mg, 0.346 mmol) and N-ethyl-diisopropylamine (146 μl, 0.864 mmol) in tetrahydrofuran (3.5 ml) was added and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo, the residue was dissolved in ethyl acetate and saturated sodium hydrogen carbonate solution and the phases were separated. The aqueous phase was extracted with ethyl acetate (3×) and the combined organic layers were washed with saturated sodium chloride solution (1×), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica) with ethyl acetate/methanol 5/1. Yield: 100 mg (64%).

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customsaturated sodium hydrogen carbonate solution and the phases were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate (3×)
  6. washthe combined organic layers were washed with saturated sodium chloride solution (1×)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (silica) with ethyl acetate/methanol 5/1

출처 및 근거

ORD 기록
ord-3d552453d4f345609c1a1e25b3935107
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268814B2

반응 노트

불러오는 중…