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Water → (R)-3-[3-(4,6-Dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester

HRID 2175181
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HRID 2175181 반응식
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[C:16]([CH3:23])[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].Br[CH2:26][C:27]1[C:31]2[C:32]([CH3:37])=[CH:33][C:34]([CH3:36])=[CH:35][C:30]=2[S:29][N:28]=1.C([O-])([O-])=[O:39].[K+].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([N:13]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:23][C:16]=2[N:15]([CH2:26][C:27]2[C:31]3[C:32]([CH3:37])=[CH:33][C:34]([CH3:36])=[CH:35][C:30]=3[S:29][N:28]=2)[C:14]1=[O:39])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 584973913-Bromomethyl-4,6-dimethyl-benzo[d]isothiazoleHCID 58497430(R)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

생성물 1

HCID 58497400(R)-3-[3-(4,6-Dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester
수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of (R)-3-(2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl)-3-phenyl-propionic acid ethyl ester (refer to example 2) (50 mg, 0.16 mmol) in DMF (10 mL) were added 3-Bromomethyl-4,6-dimethyl-benzo[d]isothiazol (62 mg, 0.24 mmol) and K2CO3 (44 mg, 0.32 mmol) at room temperature under nitrogen atmosphere. The solution was heated to 100° C. for 2 hours. The solution was cooled and water was added. The solution was extracted with EtOAc and the combined organic layer was dried with MgSO4. The solution was filtered and concentrated. The residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent to afford the title compound (15 mg, 90%) as colorless foam.

후처리

  1. temperatureThe solution was cooled
  2. extractionThe solution was extracted with EtOAc
  3. dry with materialthe combined organic layer was dried with MgSO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent

출처 및 근거

ORD 기록
ord-e2ef67f18b3f45919256e7c866c12086
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062056B2

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