Cesium carbonate → HCID 178429371、化合物

HRID 707377

反応式

HRID 707377 の反応式
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

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 51528382-Chloro-1,8-naphthyridineHCID 178429368HCID 178429368、化合物

生成物 1

HCID 178429371HCID 178429371、化合物収率 21%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e3acc8aeba6d42bd852118fa1a6a1195
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

関連ノート

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