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Triacetoxyperiodinane → 1-[5-tert-Butyl-2-(4-formyl-phenyl)-2H-pyrazol-3-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea

HRID 1402458
ノート
印刷プレビュー

反応式

HRID 1402458 の反応式
ClCCl.[C:4]([C:8]1[CH:9]=[C:10]([NH:21][C:22]([NH:24][C@@H:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C@H:28]([O:35][C:36]3[CH:37]=[CH:38][C:39]4[N:40]([C:42]([N:45]5[CH2:50][CH2:49][CH2:48][CH2:47][C@@H:46]5[CH3:51])=[N:43][N:44]=4)[CH:41]=3)[CH2:27][CH2:26]2)=[O:23])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=2)[N:12]=1)([CH3:7])([CH3:6])[CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[C:4]([C:8]1[CH:9]=[C:10]([NH:21][C:22]([NH:24][C@@H:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C@H:28]([O:35][C:36]3[CH:37]=[CH:38][C:39]4[N:40]([C:42]([N:45]5[CH2:50][CH2:49][CH2:48][CH2:47][C@@H:46]5[CH3:51])=[N:43][N:44]=4)[CH:41]=3)[CH2:27][CH2:26]2)=[O:23])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][CH:14]=2)[N:12]=1)([CH3:7])([CH3:5])[CH3:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 656671Sodium PyrosulfiteHCID 866873151-[5-tert-Butyl-2-(4-hydroxymethyl-phenyl)-2H-pyrazol-3-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea dichloromethane

生成物 1

HCID 86687314
1-[5-tert-Butyl-2-(4-formyl-phenyl)-2H-pyrazol-3-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea
収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of Intermediate 176a (1.10 g, 1.70 mmol) in DCM (25 mL) at 0° C. was added Dess-Martin periodinane (791 mg, 1.86 mmol) and the resulting red-brown solution stirred at 0° C. for 45 min. Sodium metabisulfite (920 mg), water (10 mL) and sat. aq. NaHCO3 solution (10 mL) were added and the mixture stirred at RT until gas evolution ceased (15 min). The mixture was diluted with water (25 mL) and extracted with DCM (2×25 mL). The combined organics were passed through a hydrophobic fit and concentrated in vacuo to leave the title compound as a glassy orange solid (1.10 g, 100%). LCMS (Method 3): Rt 3.91 min, m/z 647 [MH+].

後処理

  1. stirringthe mixture stirred at RT until gas evolution
  2. custom(15 min)
  3. extractionextracted with DCM (2×25 mL)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-85264d079b2b4311baac37e3504f6f44
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08907094B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート