Cesium carbonate → HCID 178429371, 화합물

HRID 707377

반응식

HRID 707377 반응식
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][C@H:13]1[CH2:16][C@H:15]([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][N:25]=[C:20]3[C:19]([CH3:27])([CH3:26])[C:18]2=[O:28])[CH2:14]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][N:5]=2)[CH:10]=[CH:11][C:2]=1[NH:12][C@H:13]1[CH2:16][C@H:15]([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][N:25]=[C:20]3[C:19]([CH3:26])([CH3:27])[C:18]2=[O:28])[CH2:14]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 51528382-Chloro-1,8-naphthyridineHCID 178429368HCID 178429368, 화합물

생성물 1

HCID 178429371HCID 178429371, 화합물수율 21%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

2-chloro-1,8-naphthyridine (89 mg, 0.54 mmol), 5-(trans-3-aminocyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (100 mg, 0.431 mmol), and cesium carbonate (202 mg, 0.620 mmol) were suspended in dry dimethylformamide (0.86 mL) under nitrogen and heated to 100° C. for 18 h. The mixture was cooled and extracted with ethyl acetate and water. The phases were separated and the organic was dried with magnesium sulfate before evaporating to dryness under reduced pressure. Purification using the ISCO (0-100% EtOAc in hexane), gave the desired 5-(trans-3-((1,8-naphthyridin-2-yl)amino)cyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (32 mg, 0.089 mmol, 21% yield) as a light yellow solid. 1H NMR (300 MHz, CHLOROFORM-d) δ: ppm 1.45 (s, 6 H) 2.42 (ddd, J=13.88, 9.28, 3.29 Hz, 2 H) 3.44-3.62 (m, 2 H) 5.22-5.38 (m, 2 H) 6.71 (d, J=8.92 Hz, 1 H) 7.16 (dd, J=7.82, 4.46 Hz, 1 H) 7.79-7.98 (m, 2 H) 8.11 (q, J=3.12 Hz, 2 H) 8.84 (dd, J=4.38, 1.90 Hz, 1 H).

후처리

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate and water
  3. customThe phases were separated
  4. dry with materialthe organic was dried with magnesium sulfate
  5. custombefore evaporating to dryness under reduced pressure
  6. customPurification

출처 및 근거

ORD 기록
ord-e3acc8aeba6d42bd852118fa1a6a1195
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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