Ethylenediamine → HCID 59333525、化合物

HRID 421341ノート

反応式

HRID 421341 の反応式
Cl[C:2]1[N:3]([CH2:25][CH:26]2[CH2:28][CH2:27]2)[C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[N:7]=[C:6]([C:17]1[C:18]([CH3:24])=[N:19][C:20]([NH2:23])=[N:21][CH:22]=1)[N:5]=2.[CH2:29]([NH2:32])[CH2:30][NH2:31].C(N(CC)CC)C.[S:40](Cl)([CH3:43])(=[O:42])=[O:41]>CN1CCCC1=O>[NH2:23][C:20]1[N:19]=[C:18]([CH3:24])[C:17]([C:6]2[N:5]=[C:4]3[C:9]([N:10]=[C:2]([NH:31][CH2:30][CH2:29][NH:32][S:40]([CH3:43])(=[O:42])=[O:41])[N:3]3[CH2:25][CH:26]3[CH2:28][CH2:27]3)=[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[N:7]=2)=[CH:22][N:21]=1

参加物

6

反応物 4

HCID 3301EthylenediamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 593334985-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-methylpyrimidin-2-amine

生成物 1

HCID 59333525HCID 59333525、化合物収率 46%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

N-Methylpyrrolidone (1 ml) was added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-methylpyrimidin-2-amine (100 mg, 0.25 mmol) and ethylenediamine (150 mg, 2.49 mmol) and the resulting mixture was stirred at 120° C. for 3.5 hours. The reaction mixture was partitioned with chloroform and saturated brine and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure, then triethylamine (100 μl, 0.75 mmol) and mesyl chloride (25 μl, 0.32 mmol) were added to the residue, and the resulting mixture was stirred for 1 hour. The reaction mixture was partitioned with ethyl acetate and water and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (57 mg, 46%) as a pale yellow solid.

後処理

  1. customThe reaction mixture was partitioned with chloroform and saturated brine
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. stirringthe resulting mixture was stirred for 1 hour
  6. customThe reaction mixture was partitioned with ethyl acetate and water
  7. washthe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid)

出典と根拠

ORDレコード
ord-70e8117407f541bfb407259b65dfb0bb
出典データセット
uspto-grants-2012_01
特許番号
US08097622B2

反応ノート

読み込み中…