4-Methylmorpholine → 1-(4-(5'-Chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one

HRID 2172860ノート

反応式

HRID 2172860 の反応式
[Cl:1][C:2]1[C:3]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][N:15]=2)=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.[CH3:50][S:51]([CH2:54][CH2:55][C:56](O)=[O:57])(=[O:53])=[O:52]>C(Cl)Cl.C(Cl)Cl.CO>[Cl:1][C:2]1[C:3]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][N:15]=2)=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:56](=[O:57])[CH2:55][CH2:54][S:51]([CH3:50])(=[O:53])=[O:52])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1203083-(Methylsulfonyl)propanoic acidHCID 675095955'-Chloro-3,5-dimethyl-2'-(piperazin-1-yl)-2,4'-bipyridine

生成物 1

HCID 569562401-(4-(5'-Chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one収率 90%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

To a solution of 5′-chloro-3,5-dimethyl-2′-(piperazin-1-yl)-2,4′-bipyridine (2.3 g, 15.1 mmol) and HOBT (2.55 g, 18.9 mmol) in CH2Cl2 (60 mL) was added NMM (5.67 g, 56.7). After stirring for 30 min at room temperature, EDCI (3.63 g, 18.9 mmol) and 3-(methylsulfonyl)propanoic acid (3.9 g, 12.6 mmol) were added and the mixture was stirred at 30° C. for 18 hours. TLC (CH2Cl2/MeOH=10:1) showed the starting material was consumed completely. After removal of the solvent in vacuo, the residue was dissolved in CH2Cl2 (180 mL), washed with saturated aq. NaHCO3 (40 mL), saturate aq. NH4Cl (40 mL) and brine (40 mL). The resulting material was dried over Na2SO4 and concentrated in vacuo to give title compound (4.8 g, 90%) as white solid. 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 8.15 (s, 1H), 7.36 (s, 1H), 6.53 (s, 1H), 3.69-3.66 (m, 2H), 3.58-5.53 (m, 4H), 3.48-3.46 (m, 2H), 3.41-3.37 (m, 2H), 2.94 (s, 3H) 2.89-2.86 (m, 2H), 2.31 (s, 3H), 2.10 (s, 3H); m/z for C20H25ClN4O3S 437.3 (M+H)+.

後処理

  1. stirringthe mixture was stirred at 30° C. for 18 hours
  2. customwas consumed completely
  3. customAfter removal of the solvent in vacuo
  4. dissolutionthe residue was dissolved in CH2Cl2 (180 mL)
  5. washwashed with saturated aq. NaHCO3 (40 mL)
  6. concentrationsaturate aq. NH4Cl (40 mL) and brine (40 mL)
  7. dry with materialThe resulting material was dried over Na2SO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f95d3b1a3b2045039ac902fb703ad4b9
出典データセット
uspto-grants-2015_06
特許番号
US09056865B2

反応ノート

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