Acetic Acid → 5-(3-{[[2-(tert-Butoxycarbonyl-methyl-amino)-ethyl]-(3-fluoro-benzyl)-amino]-methyl}-4-fluoro-phenyl)-indazole-1-carboxylic acid tert-butyl ester

HRID 1864794ノート

反応式

HRID 1864794 の反応式
C(O[BH-](O[C:11](=O)[CH3:12])OC(=O)C)(=O)C.[Na+].[C:15](O)(=O)C.[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[C:37]([CH2:42][NH:43][CH2:44][CH2:45][N:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH3:47])[CH:36]=3)=[CH:32][CH:33]=2)[CH:28]=[N:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].[F:55][C:56]1[CH:63]=CC(C=O)=[CH:58][CH:57]=1>ClC(Cl)C.O>[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[C:37]([CH2:42][N:43]([CH2:44][CH2:45][N:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH3:47])[CH2:15][C:11]4[CH:12]=[CH:58][CH:57]=[C:56]([F:55])[CH:63]=4)[CH:36]=3)=[CH:32][CH:33]=2)[CH:28]=[N:27]1)=[O:25])([CH3:21])([CH3:22])[CH3:20]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 687486135-(3-{[2-(tert-Butoxycarbonyl-methyl-amino)-ethylamino]-methyl}-4-fluoro-phenyl)-indazole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 687474165-(3-{[[2-(tert-Butoxycarbonyl-methyl-amino)-ethyl]-(3-fluoro-benzyl)-amino]-methyl}-4-fluoro-phenyl)-indazole-1-carboxylic acid tert-butyl ester収率 74.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

Sodium triacetoxyborohydride (254 mg, 1.2 mmol) and acetic acid (48 mg, 0.8 mmol) were added to a mixture of 5-(3-{[2-(tert-butoxycarbonyl-methyl-amino)-ethylamino]-methyl}-4-fluoro-phenyl)-indazole-1-carboxylic acid tert-butyl ester (400 mg, 0.8 mmol) and 4-fluorobenzaldehyde (99 mg, 0.8 mmol) in 15 mL of dichloroethane. The mixture was stirred at ambient temperature for 80 h, and then it was diluted with water, the layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were washed with sequentially with water, saturated sodium bicarbonate solution and water, dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with ethyl acetate/pentane) provided 360 mg of product. LC/MS: Retention time, 4.10 min; (M+H)=607.

後処理

  1. customthe layers were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. washThe combined organic layers were washed with sequentially with water, saturated sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto leave the crude product
  8. washChromatography (elution with ethyl acetate/pentane)

出典と根拠

ORDレコード
ord-8e905ddf8d0c4ab4b51cc3dea0f0bf46
出典データセット
uspto-grants-2009_12
特許番号
US07625889B2

反応ノート

読み込み中…