Phenylacetyl chloride → 2-(4-(Morpholine-4-carbonyl)phenylamino)-6-(4-(2-phenylacetyl)piperazin-1-yl)nicotinamide

HRID 2044047ノート

反応式

HRID 2044047 の反応式
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:24]=[C:23]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:22]=[CH:21][C:17]=3[C:18]([NH2:20])=[O:19])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CCN(CC)CC.[C:38]1([CH2:44][C:45](Cl)=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1.C(Cl)Cl>[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:24]=[C:23]([N:25]4[CH2:30][CH2:29][N:28]([C:45](=[O:46])[CH2:44][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH2:27][CH2:26]4)[CH:22]=[CH:21][C:17]=3[C:18]([NH2:20])=[O:19])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 498463872-(4-(Morpholine-4-carbonyl)phenylamino)-6-(piperazin-1-yl)nicotinamide

生成物 1

HCID 574896042-(4-(Morpholine-4-carbonyl)phenylamino)-6-(4-(2-phenylacetyl)piperazin-1-yl)nicotinamide収率 38.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 2-(4-(morpholine-4-carbonyl)phenylamino)-6-(piperazin-1-yl)nicotinamide (28 mg, 0.068 mmol) and Et3N (0.019 mL, 0.136 mmol) in THF (2 mL) and CH2Cl2 (2.000 mL) was added 2-phenylacetyl chloride (10.55 mg, 0.068 mmol). The reaction mixture was stirred at rt for 10 min, diluted with CH2Cl2, washed with satd NaHCO3, separated, and concentrated. The residue was purified by prep-HPLC. The product containing fractions were collected, basified with 1N NaOH, extracted with CH2Cl2, separated, and concentrated to give 14 mg of 2-(4-(morpholine-4-carbonyl)phenylamino)-6-(4-(2-phenylacetyl)piperazin-1-yl)nicotinamide as a white solid. LCMS: (M+H)+=529.40. 1H NMR (400 MHz, CDCl3) δ ppm 11.17 (1H, s), 7.63 (2H, d, J=8.56 Hz), 7.55 (1H, d, J=8.81 Hz), 7.35-7.40 (2H, m), 7.31-7.35 (2H, m), 7.23-7.31 (3H, m), 5.99 (1H, d, J=8.81 Hz), 5.59 (2H, s), 3.50-3.81 (18H, m).

後処理

  1. washwashed with satd NaHCO3
  2. customseparated
  3. concentrationconcentrated
  4. customThe residue was purified by prep-HPLC
  5. additionThe product containing fractions
  6. customwere collected
  7. extractionextracted with CH2Cl2
  8. customseparated
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-210c26547d5145648cc0aee66acf8bd9
出典データセット
uspto-grants-2013_11
特許番号
US08586751B2

反応ノート

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