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Hydrochloric Acid → Ammonium Hydroxide

HRID 1630788
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HRID 1630788 반응식
[I-].[Li+].C([O:5][C:6](=[O:33])[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[C:17]([CH3:25])=[C:16]2[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:9][C:8]=1[CH3:32])C.Cl>N1C(C)=CC=CC=1C>[NH4+:15].[OH-:5].[CH3:13][C:12]1[CH:11]=[C:10]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[C:17]([CH3:25])=[C:16]2[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:9]=[C:8]([CH3:32])[C:7]=1[C:6]([OH:33])=[O:5]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 582156242,6-Dimethyl-4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid ethyl ester

생성물 2

HCID 14923Ammonium Hydroxide수율 0.1%HCID 582155892,6-Dimethyl-4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid

시약·촉매·용매 1

HCID 79372,6-Lutidine용매

실험 절차

To a refluxing solution of lithium iodide (0.218 g, 1.626 mmol) in 2,6-lutidine (5 mL) is added 2,6-dimethyl-4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid ethyl ester (0.176 g, 0.407 mmol). The reaction is refluxed overnight. It is cooled to room temperature, acidified to pH 1 using 1M aqueous HCl solution and extracted with dichloromethane. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by reverse phase HPLC with Xbridge Shield RP18 column and a 0.1% aqueous NH4OH in acetonitrile gradient to afford 2,6-dimethyl-4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid as a solid. 1H NMR (400 MHz, MeOD) δ ppm 2.22 (s, 6H), 2.28 (s, 3H), 5.22 (s, 2H), 6.49 (s, 2H), 7.15 (dd, J=8.6, 2.0 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.51-7.57 (m, 1H), 7.61 (d, J=1.8 Hz, 1H), 7.81 (dt, J=8.1, 2.0, 1.8 Hz, 1H), 8.58 (d, J=1.3 Hz, 1H), 8.61 (dd, J=4.9, 1.6 Hz, 1H). HRMS (ESI) m/z 405.1379 [(M+H)+ Calcd for C24H21ClN2O2: 405.1370].

후처리

  1. temperatureThe reaction is refluxed overnight
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by reverse phase HPLC with Xbridge Shield RP18 column

출처 및 근거

ORD 기록
ord-0b8388200cb54e3bbca92bd17c509ab3
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08791141B2

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