Hydrochloric Acid → 1-{2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl}-5-(2-methoxyethoxy)-N-[1-(propan-2-yl)piperidin-4-yl]-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 2250445노트

반응식

HRID 2250445 반응식
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[NH:26][C:16]3=[CH:17][N:18]=[C:19]([O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:20]=[C:15]3[CH:14]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].CN(C=O)C.Br[CH2:33][C:34]([NH:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=1)=[O:35].Cl>O.CC#N>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([NH:10][C:11]([C:13]2[N:26]([CH2:33][C:34](=[O:35])[NH:36][C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=3)[C:16]3=[CH:17][N:18]=[C:19]([O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:20]=[C:15]3[CH:14]=2)=[O:12])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 865958665-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

생성물 1

HCID 533163881-{2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl}-5-(2-methoxyethoxy)-N-[1-(propan-2-yl)piperidin-4-yl]-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

시약·촉매·용매 1

HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

To a solution of 461 mg (1.27 mmol) ) 5-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide in 20 mL absolute DMF 46 mg (1.91 mmol) NaH (96%) were added in an argon atmosphere. The mixture was stirred for 15 min. at room temperature. 479 mg (1.91 mmol) 2-Bromo-N-(5-chloro-pyridin-2-yl)-acetamide were added and the mixture stirred for 3 h at room temperature. The solvent was removed in vacuo, the residue dissolved in CH2Cl2 and the CH2Cl2 phase washed with H2O and dried over Na2SO4. After filtration, the organic phase was concentrated and the residue purified by chromatography over silica gel using CH2Cl2/MeOH/HOAc/H2O=90/10/1/1 as eluent followed by preparative HPLC (eluent: CH3CN/H2O/0.1% CF3COOH). The fractions containing the product were combined and concentrated in vacuo. The residue was lyophilized with 2 equivalents 1N HCl in a H2O/CH3CN mixture yielding the hydrochloride salt of the desired product.

후처리

  1. stirringthe mixture stirred for 3 h at room temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in CH2Cl2
  4. washthe CH2Cl2 phase washed with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration
  7. concentrationthe organic phase was concentrated
  8. customthe residue purified by chromatography over silica gel
  9. additionThe fractions containing the product
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fa09a2c0bb344f8791fdcc06e66a38bb
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07317027B2

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