2-(Methylamino)ethanol → 4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-N-(2-hydroxy-ethyl)-N-methyl-2-nitro-benzamide

HRID 551864

反応式

HRID 551864 の反応式
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[C:11]([N+:18]([O-:20])=[O:19])[CH:10]=2)[C:5](=[O:21])[N:4]([CH3:22])[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH3:59][NH:60][CH2:61][CH2:62][OH:63]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([N:60]([CH2:61][CH2:62][OH:63])[CH3:59])=[O:15])=[C:11]([N+:18]([O-:20])=[O:19])[CH:10]=2)[C:5](=[O:21])[N:4]([CH3:22])[CH:3]=1

参加物

6

反応物 4

HCID 80162-(Methylamino)ethanolHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 587290444-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-2-nitro-benzoic acid

生成物 1

HCID 587290674-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-N-(2-hydroxy-ethyl)-N-methyl-2-nitro-benzamide収率 90.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-2-nitro-benzoic acid (3) (1.0 g, 2.72 mmol), (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate [BOP] (120 mg, 2.72 mmol,), diisopropylethylamine (1.42 mL, 8.15 mmol) and 2-methylaminoethanol (0.33 mL, 4.07 mmol) are dissolved in DMF (25 mL) at room temperature and allowed to react for 60 min. The reaction is quenched by the addition of water (120 mL) and the resulting suspension was allowed to stir for 15 min. The suspension is then filtered, washed with water (3×50 mL) and then air-dried to give 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-N-(2-hydroxy-ethyl)-N-methyl-2-nitro-benzamide (4) as a yellow solid (1.05 g).

後処理

  1. customto react for 60 min
  2. customThe reaction is quenched by the addition of water (120 mL)
  3. filtrationThe suspension is then filtered
  4. washwashed with water (3×50 mL)
  5. customair-dried

出典と根拠

ORDレコード
ord-ddd3e58f58504990bb68debb15943e83
出典データセット
uspto-grants-2011_05
特許番号
US07947835B2

関連ノート

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