Dimethyl Sulfoxide → HCID 16066664、化合物

HRID 1896201ノート

反応式

HRID 1896201 の反応式
Cl[C:2]1[N:3]=[C:4]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([CH2:16][CH3:17])[C:6]=2[N:7]=1.[NH:26]1[CH2:34][CH2:33][CH:29]([C:30]([OH:32])=[O:31])[CH2:28][CH2:27]1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>C(OCC)(=O)C.O>[CH2:14]([O:13][CH2:12][CH2:11][N:10]1[C:5]2[C:4]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=3)=[N:3][C:2]([N:26]3[CH2:34][CH2:33][CH:29]([C:30]([OH:32])=[O:31])[CH2:28][CH2:27]3)=[N:7][C:6]=2[C:8]([CH2:16][CH3:17])=[N:9]1)[CH3:15]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 37734-Piperidinecarboxylic acidHCID 10796Cesium carbonateHCID 16222003HCID 16222003、化合物

生成物 1

HCID 16066664HCID 16066664、化合物収率 7.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
125 °C

実験手順

A mixture of N-[5-chloro-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl]-4-methylpyridin-2-ylamine from step 5 (5.42 g, 166 mmol), isonipecotic acid (85.9 g, 665 mmol), cesium carbonate (162 g, 498 mmol), and DMSO (55 mL) was heated, with stirring, at 125° C. After 20 h, the mixture was cooled to 20° C. and water (165 mL) was added. The mixture was stirred for 15 min and was then treated with ethyl acetate (55 mL). The layers were separated and the aqueous was treated with another portion of ethyl acetate (55 mL). The layers were separated again and the aqueous layer was taken to pH ˜5 using 6 M HCl. After stirring for 1 hour, the resulting solid was filtered, washed with water (20 mL) and dried in vacuuo, to give 5.5 g of the title compound. 1H NMR (400 MHz, DMSO-d6): 1.10 (t, 3 H), 1.30 (t, 3 H), 1.49-1.60 (m, 2 H), 1.84-1.95 (m, 2 H), 2.32-2.36 (m, 3 H), 2.52-2.57 (m, 1 H), 2.78 (q, 2 H), 2.99-3.08 (m, 2 H), 3.52 (q, 2 H), 3.78 (t, 2 H), 4.45-4.53 (m, 2 H), 4.56-4.64 (m, 2 H), 6.91 (d, 1 H), 8.05 (s, 1 H), 8.18 (d, 1 H), 9.63 (s, 1 H), 12.18 (s, 1 H). LCMS m/z 454.

後処理

  1. temperaturewas heated
  2. temperaturethe mixture was cooled to 20° C.
  3. stirringThe mixture was stirred for 15 min
  4. customThe layers were separated
  5. additionthe aqueous was treated with another portion of ethyl acetate (55 mL)
  6. customThe layers were separated again
  7. stirringAfter stirring for 1 hour
  8. filtrationthe resulting solid was filtered
  9. washwashed with water (20 mL)
  10. customdried in vacuuo

出典と根拠

ORDレコード
ord-c7e7fae5a23443c3af97eb598edfc341
出典データセット
uspto-grants-2013_08
特許番号
US08518956B2

反応ノート

読み込み中…