Ethylamine → N-ethyl-5-methyl-6-[7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pyrimidin-4-amine

HRID 241218ノート

反応式

HRID 241218 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:14][C:13]3[CH:15]=[C:16]([C:19]4[CH:20]=[C:21]5[NH:27][C:26]([CH3:28])=[N:25][C:22]5=[N:23][CH:24]=4)[CH:17]=[CH:18][C:12]=3[O:11][CH2:10][CH2:9]2)[C:3]=1[CH3:29].[CH2:30]([NH2:32])[CH3:31]>CN1CCCC1=O.C(OCC)(=O)C>[CH2:30]([NH:32][C:2]1[C:3]([CH3:29])=[C:4]([N:8]2[CH2:14][C:13]3[CH:15]=[C:16]([C:19]4[CH:20]=[C:21]5[NH:27][C:26]([CH3:28])=[N:25][C:22]5=[N:23][CH:24]=4)[CH:17]=[CH:18][C:12]=3[O:11][CH2:10][CH2:9]2)[N:5]=[CH:6][N:7]=1)[CH3:31]

参加物

5

反応物 2

HCID 6341EthylamineHCID 595865474-(6-chloro-5-methylpyrimidin-4-yl)-7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

生成物 1

HCID 59586184N-ethyl-5-methyl-6-[7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pyrimidin-4-amine収率 30%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A suspension of 4-(6-chloro-5-methylpyrimidin-4-yl)-7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (44 mg, 0.11 mmol), and ethylamine (29 mg, 0.65 mmol), in N-methylpyrrolidinone (2 mL) was stirred at 100° C. for 6 h. The reaction mixture was diluted with ethyl acetate (75 mL), washed with saturated sodium bicarbonate (75 mL) and brine (50 mL), and dried over sodium sulfate. Concentration and purification by preparatory HPLC (0.1% aqueous ammonium acetate-acetonitrile) gave N-ethyl-5-methyl-6-[7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pyrimidin-4-amine (13 mg, 30% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.50 (s, 1H), 8.07 (s, 1H), 8.04 (d, 1H), 7.56-7.48 (m, 2H), 7.11 (d, 1H), 4.57 (s, 2H), 4.33 (d, 2H), 3.79 (d, 2H), 3.53-3.39 (q, 2H), 2.64 (s, 3H), 2.04 (s, 3H), 1.21 (t, 3H); MS (EI) for C23H25N7O: 416 (MH+).

後処理

  1. washwashed with saturated sodium bicarbonate (75 mL) and brine (50 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration and purification by preparatory HPLC (0.1% aqueous ammonium acetate-acetonitrile)

出典と根拠

ORDレコード
ord-3ac49b21e3c74f479a8afe533058a085
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

反応ノート

読み込み中…