Cesium carbonate → HCID 70817658, 화합물

HRID 82104

반응식

HRID 82104 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[NH:22][CH:21]=3)=[O:19])[CH:17]=2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:36][C:37]([NH2:39])=[O:38]>CN(C=O)C>[NH2:39][C:37](=[O:38])[CH2:36][N:22]1[C:23]2[N:24]=[CH:25][N:26]=[CH:27][C:28]=2[C:20]([C:18]([C:16]2[CH:17]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:13]=[N:14][CH:15]=2)=[O:19])=[CH:21]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 708176452-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide

생성물 1

HCID 70817658HCID 70817658, 화합물수율 59%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide (Example 308, 50 mg, 0.13 mmol) in DMF (1 ml) was added Cs2CO3 (75 mg, 0.23 mmol) followed by 2-bromoacetamide (21.3 mg, 0.154 mmol). The reaction was then stirred at room temperature overnight. The reaction was quenched with water (5 mL) and extracted with EtOAc (3×5 mL). The organics were combined, washed with water (5 mL) then brine (5 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification by preparative HPLC gave the title compound in 59% yield, 34 mg.

후처리

  1. customThe reaction was quenched with water (5 mL)
  2. extractionextracted with EtOAc (3×5 mL)
  3. washwashed with water (5 mL)
  4. dry with materialbrine (5 mL), dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-49952a09578e4a01a44231957fd0b892
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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