Ammonium Chloride → 3-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-4-methyl-benzamide

HRID 337030노트

반응식

HRID 337030 반응식
[Cl:1][C:2]1[N:3]=[C:4]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11](OC)=[O:12])[CH:7]=1.[CH:27]1([NH2:30])[CH2:29][CH2:28]1.C([Mg]Cl)(C)C.[NH4+].[Cl-]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11]([NH:30][CH:27]2[CH2:29][CH2:28]2)=[O:12])[CH:7]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 69828CyclopropylamineHCID 866632373-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl esterHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 666864943-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-4-methyl-benzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 3-[5-chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester (Example 107b) in tetrahydrofuran (6 mL) under nitrogen was added cyclopropylamine (0.15 mL) followed by iso-propylmagnesium chloride (2M in tetrahydrofuran, 0.8 mL), portionwise. After 1 h, sat. aqueous NH4Cl was added and the mixture extracted into ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo. Purification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent) afforded the title compound (35 mg).

후처리

  1. extractionthe mixture extracted into ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customPurification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent)

출처 및 근거

ORD 기록
ord-2e32a65835c44e32bbf56ad3a7531f9f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889692B2

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