Triethylamine → Methyl 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylate

HRID 449338ノート

反応式

HRID 449338 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[NH2:8][C:9]1[N:18]=[C:17](Cl)[C:16]2[C:11](=[CH:12][C:13]([C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:15]=2)[N:10]=1.C(N(CC)CC)C>C(O)C>[NH2:8][C:9]1[N:18]=[C:17]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[C:16]2[C:11](=[CH:12][C:13]([C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:15]=2)[N:10]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 59496646Methyl 2-amino-4-chloroquinazoline-7-carboxylate

生成物 1

HCID 59496531Methyl 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylate収率 63.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
110 °C

実験手順

1-Methyl-piperazine (210 uL, 1.9 mmol) was added to a mixture of methyl 2-amino-4-chloroquinazoline-7-carboxylate (300 mg, 1 mmol) in ethanol (3 mL) and triethylamine (350 μL, 2.5 mmol). The mixture was heated in an oil bath at 110° C. for 1 h. The reaction mixture was concentrated to remove the ethanol and was partitioned between water and EtOAc. The organic phase was washed with saturated NaCl aqueous solution, dried over MgSO4, filtered, and concentrated to give the crude product, (190 mg, 50%) as an off white amorphous solid. 1H NMR (300 MHz, DMSO) δ 2.23 (s, 3H), 3.56 (m, 4H), 3.86 (s, 3H), 3.90 (m, 4H), 6.53 (b, 2H), 7.50 (d, 1H), 7.80 (m, 2H); Analytic LCMS (M+H)+: m/z=302.1.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the ethanol
  3. customwas partitioned between water and EtOAc
  4. washThe organic phase was washed with saturated NaCl aqueous solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-a21a01cf26c54a7db3f3c61f84f30c47
出典データセット
uspto-grants-2013_07
特許番号
US08481732B2

反応ノート

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