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Ammonium Chloride → HCID 66778073, 화합물

HRID 2091322
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HRID 2091322 반응식
[CH:1]1([CH:7]([NH:18][C:19]2[CH:27]=[CH:26][C:22](C(O)=O)=[CH:21][CH:20]=2)[C:8]2[S:16][C:15]3[C:10](=N[CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][NH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].[OH2:37].ON1C2C=CC=C[C:42]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+:61]>CN(C)C=O.C(N(CC)CC)C>[CH:1]1([CH:7]([NH:18][C:19]2[CH:27]=[CH:26][C:22]([C:28]([N:29]([CH3:42])[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:37])=[CH:21][CH:20]=2)[C:8]2[S:16][C:15]3[C:10](=[N:61][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667781814-{[Cyclohexyl(3-methylthieno[3,2-b]pyridin-2-yl)methyl]amino}benzoic acid

생성물 1

HCID 66778073
HCID 66778073, 화합물
수율 84%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a mixture of 4-{[cyclohexyl(3-methylthieno[3,2-b]pyridin-2-yl)methyl]amino}benzoic acid (300 mg) synthesized in Example A144(5), ethyl 3-(methylamino)propanoate (155 mg), 1-hydroxybenzotriazole monohydrate (181 mg), triethylamine (329 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (226 mg), and the mixture was stirred at room temperature for 1 day. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50-100% ethyl acetate/hexane) to give the title object compound (325 mg, 84%) as a pale-yellow oil.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (50-100% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-a68e2d43737b463a8784a6d684cd9475
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436043B2

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