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Tetrahydrofuran → 1-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide

HRID 1025586
ノート
印刷プレビュー

反応式

HRID 1025586 の反応式
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH2:44][OH:45])=[C:18]([N:22]3[CH:26]=[C:25]([C:27]#[N:28])[C:24]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]([N:38]5[CH2:43][CH2:42][O:41][CH2:40][CH2:39]5)=[O:37])=[CH:32][CH:31]=4)=[N:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C1C[O:49]CC1>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH2:44][OH:45])=[C:18]([N:22]3[CH:26]=[C:25]([C:27]([NH2:28])=[O:49])[C:24]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]([N:38]5[CH2:39][CH2:40][O:41][CH2:42][CH2:43]5)=[O:37])=[CH:32][CH:31]=4)=[N:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 8028TetrahydrofuranHCID 710083501-[3-(6-tert-Butyl-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl]-3-[4-(morpholine-4-carbonyl)phenylamino]-1H-pyrazole-4-carbonitrile

生成物 1

HCID 710082871-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide収率 76.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

1-[3-(6-tert-Butyl-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl]-3-[4-(morpholine-4-carbonyl)phenylamino]-1H-pyrazole-4-carbonitrile (52 mg, 0.0861 mmol) was dissolved in 4 mL of THF and 0.4 mL of water. Then dihydrogen tris(dimethylphosphinito)hydroplatinate (CAS#173416-05-2, 3 mg, 8% eq) was added. The mixture was refluxed for 1 hr. TLC indicated complete consumption of the starting material. LC/MS indicated the clean product formed with the correct MW. The mixture was evaporated to dryness and then dissolved in dichloromethane, dried over sodium sulfate and filtered. After the evaporation of solvents, the residue was purified through flash column chromatography (24 g silica gel, methanol in dichloromethane, 0% to 5% in 16 minutes) to give 1-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide as a white solid (41 mg, 76.6% yield). LC/MS clacd for C34H35N7O5 (m/e) 621.27, obsd 622.1 (M+H, ES+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41 (s, 9H) 3.41-3.71 (m, 8H), 4.37 (br. s., 2H), 4.74 (br. s., 1H), 7.36 (d, J=6.3 Hz, 3H), 7.49-7.71 (m, 5H), 7.80 (br. s., 1H), 8.04 (d, J=9.1 Hz, 2H), 8.25 (d, J=6.6 Hz, 1H), 8.56 (br. s., 2H), 9.44 (br. s., 1H).

後処理

  1. temperatureThe mixture was refluxed for 1 hr
  2. customconsumption of the starting material
  3. customformed with the correct MW
  4. customThe mixture was evaporated to dryness
  5. dissolutiondissolved in dichloromethane
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customAfter the evaporation of solvents
  9. customthe residue was purified through flash column chromatography (24 g silica gel, methanol in dichloromethane, 0% to 5% in 16 minutes)

出典と根拠

ORDレコード
ord-8057a0d1728841c3b9fea247bf0e5280
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08729078B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート