Water → 5-(1-(Benzo[D]thiazol-2-YL)piperidin-4-YL)-7,7-dimethyl-5H-pyrrolo[2,3-B]pyrazin-6(7H)-one

HRID 707394ノート

反応式

HRID 707394 の反応式
Cl.[CH3:2][C:3]1([CH3:19])[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[N:5]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:4]1=[O:18].C(=O)([O-])[O-].[K+].[K+].Cl[C:27]1[S:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1.O>CS(C)=O>[S:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[N:15]1[CH2:16][CH2:17][CH:12]([N:5]2[C:6]3=[N:7][CH:8]=[CH:9][N:10]=[C:11]3[C:3]([CH3:19])([CH3:2])[C:4]2=[O:18])[CH2:13][CH2:14]1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 119872-ChlorobenzothiazoleHCID 866941487,7-Dimethyl-5-(piperidin-4-YL)-5H-pyrrolo[2,3-B]pyrazin-6(7H)-one hydrochloride2 回

生成物 1

HCID 866942595-(1-(Benzo[D]thiazol-2-YL)piperidin-4-YL)-7,7-dimethyl-5H-pyrrolo[2,3-B]pyrazin-6(7H)-one収率 47%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 7,7-dimethyl-5-(piperidin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one hydrochloride (Intermediate 78) (0.107 g, 0.378 mmol), potassium carbonate (0.183 g, 1.324 mmol), and 2-chlorobenzo[d]thiazole (0.077 g, 0.454 mmol) in DMSO (3 mL) was heated at 110° C. in 2 h. The reaction mixture was cooled, H2O was added, and extracted with DCM (3×). The organic extracts were dried over Na2SO4, filtered, concentrated, and purified by reverse phase HPLC. The pure fractions were concentrated to minimal H2O, neutralized with saturated aqueous NaHCO3. The white solid was collected, washed with H2O, and dried to afford the title compound (67 mg, 47%). MS (M+1): 380. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.04-8.19 (2 H, m), 7.77 (1 H, d, J=7.4 Hz), 7.46 (1 H, d, J=8.0 Hz), 7.21-7.35 (1 H, m), 6.98-7.14 (1 H, m), 4.46-4.65 (1 H, m), 4.18 (2 H, d, J=13.1 Hz), 3.32-3.41 (2 H, m), 2.52-2.62 (2 H, m), 1.83 (2 H, d, J=10.8 Hz), 1.33 (6 H, s)

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM (3×)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by reverse phase HPLC
  7. concentrationThe pure fractions were concentrated to minimal H2O
  8. customThe white solid was collected
  9. washwashed with H2O
  10. customdried

出典と根拠

ORDレコード
ord-be48f53c58e24ec39390271732eeeca3
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

反応ノート

読み込み中…