Triethylamine → HCID 178493751, 화합물

HRID 869638노트

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HRID 869638 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([C@H:21]2[CH2:26][CH2:25][C@H:24]([C:27]([F:30])([F:29])[F:28])[CH2:23][CH2:22]2)=[O:20])[C:6]([C:9](O)=[O:10])=[N:7][CH:8]=1.[Cl-].[NH4+].Cl.C([N:36]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([C@H:21]2[CH2:22][CH2:23][C@H:24]([C:27]([F:28])([F:29])[F:30])[CH2:25][CH2:26]2)=[O:20])[C:6]([C:9]([NH2:36])=[O:10])=[N:7][CH:8]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178493765HCID 178493765, 화합물

생성물 1

HCID 178493751HCID 178493751, 화합물수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-methoxy-3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinic acid (150 mg, 0.35 mmol, EXAMPLE 31 Step 4) and ammonium chloride (56 mg, 1.05 mmol) in dichloromethane (5 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) (100 mg, 0.52 mmol), 1-hydroxybenzotriazole hydrate (HOBt) (53 mg, 0.35 mmol) and triethylamine (176 mg, 1.74 mmol) respectively. After being stirred at room temperature for 24 h, water was added to the mixture. The mixture was extracted with dichloromethane, and the extract was dried over sodium sulfate and concentrated in vacuo to afford an oil. The residual oil was purified by NH gel column chromatography (methanol/dichloromethane 1:30) followed by preparative high pressure liquid chromatography (prep. HPLC) (acetonitrile/0.01% aq. ammonia 96:4 to 4:96) to afford 75 mg (50%) of the title compound as an amorphous powder.

후처리

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialthe extract was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto afford an oil
  5. customThe residual oil was purified by NH gel column chromatography (methanol/dichloromethane 1:30)

출처 및 근거

ORD 기록
ord-1f8fb741eb55432284dd5aff8c670ee9
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969383B2

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