Water → {Methyl-[7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonyl]-amino}-acetic acid methyl ester

HRID 589966노트

반응식

HRID 589966 반응식
C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:29])(=[O:28])[NH:26][CH3:27])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:36][O:37][C:38](=[O:41])[CH2:39]Cl.O>CN(C=O)C>[CH3:36][O:37][C:38](=[O:41])[CH2:39][N:26]([CH3:27])[S:25]([N:20]1[CH2:19][CH2:18][N:17]([C:16]2[C:11]3[CH:10]=[CH:9][NH:8][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:24][C:21]21[CH2:22][CH2:23]2)(=[O:28])=[O:29]

참가 물질

6

반응물 4

HCID 962WaterHCID 7295Methyl chloroacetateHCID 10796Cesium carbonateHCID 682959194-(4-Methylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester2회

생성물 1

HCID 57410569{Methyl-[7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonyl]-amino}-acetic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

4-(4-Methylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 4) (0.047 mmol) was dissolved in dry DMF (0.5 mL) and added Cs2CO3 (0.071 mmol) and chloro-acetic acid methyl ester (0.071 mmol). Stirred at 40° C. for 2 h and then added H2O (1.5 mL). Extracted with EtOAc (3×1 mL) and the combined organic phases were washed with brine (1 mL) and concentrated in vacuo. The residual oil was treated with TFA (1 mL) at rt for 1 h. The crude reaction mixture was concentrated in vacuo and redissolved in DMSO (0.5 mL). The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

후처리

  1. extractionExtracted with EtOAc (3×1 mL)
  2. washthe combined organic phases were washed with brine (1 mL)
  3. concentrationconcentrated in vacuo
  4. additionThe residual oil was treated with TFA (1 mL) at rt for 1 h
  5. customThe crude reaction mixture
  6. concentrationwas concentrated in vacuo
  7. dissolutionredissolved in DMSO (0.5 mL)
  8. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

출처 및 근거

ORD 기록
ord-0f4a5bbf95aa4293b71f4ae633e5df0d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233964B2

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