Water → 4-{4-[Bis-(3-cyano-propyl)-sulfamoyl]-4,7-diaza-spiro[2.5]oct-7-yl}-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

HRID 589947노트

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HRID 589947 반응식
[C:1]([O:5][C:6]([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:28])(=[O:27])[NH2:26])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:36][CH2:37][CH2:38][C:39]#[N:40].O>CN(C=O)C>[C:1]([O:5][C:6]([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:27])(=[O:28])[N:26]([CH2:12][CH2:11][CH2:10][C:9]#[N:8])[CH2:36][CH2:37][CH2:38][C:39]#[N:40])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 682960294-(4-Sulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester2회

생성물 1

HCID 682960054-{4-[Bis-(3-cyano-propyl)-sulfamoyl]-4,7-diaza-spiro[2.5]oct-7-yl}-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

4-(4-Sulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 2) (112 mg, 0.27 mmol) was dissolved in dry DMF (2 ml), added K2CO3 (38 mg, 0.27 mmol) and cooled to 0° C. A solution of 4-bromobutyronitrile (40 mg, 0.27 mmol) in dry DMF (0.5 mL) was added and the reaction mixture was stirred at rt for 16 h. The crude mixture was treated with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic phases were washed with H2O (2×10 mL), brine (2×10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The products were purified by flash chromatography on silica using EtOAc in heptane as eluent.

후처리

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined organic phases were washed with H2O (2×10 mL), brine (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe products were purified by flash chromatography on silica

출처 및 근거

ORD 기록
ord-ab45fd09a9224e2a925495e8c2c90e37
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233964B2

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