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

HRID 1864793노트

반응식

HRID 1864793 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(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]([CH:42]=O)[CH:36]=3)=[CH:32][CH:33]=2)[CH:28]=[N:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].[C:44]([O:48][C:49](=[O:55])[N:50]([CH2:52][CH2:53][NH2:54])[CH3:51])([CH3:47])([CH3:46])[CH3:45]>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][NH:54][CH2:53][CH2:52][N:50]([C:49]([O:48][C:44]([CH3:47])([CH3:45])[CH3:46])=[O:55])[CH3:51])[CH:36]=3)=[CH:32][CH:33]=2)[CH:28]=[N:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 2756424N-Boc-N-methylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 866164695-(4-Fluoro-3-formylphenyl)-indazole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 687486135-(3-{[2-(tert-Butoxycarbonyl-methyl-amino)-ethylamino]-methyl}-4-fluoro-phenyl)-indazole-1-carboxylic acid tert-butyl ester수율 100.3%

시약·촉매·용매 2

HCID 962Water용매HCID 63651,1-Dichloroethane용매

실험 절차

Sodium triacetoxyborohydride (250 mg, 1.2 mmol) and acetic acid (42 mg, 1.2 mmol) were added to a mixture of 5-(4-fluoro-3-formylphenyl)-indazole-1-carboxylic acid tert-butyl ester (270 mg, 0.8 mmol) and (2-amino-ethyl)-methyl-carbamic acid tert-butyl ester (210 mg, 1.2 mmol) in 8 mL of dichloroethane. The mixture was stirred at ambient temperature overnight, 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 methanol/dichloromethane) provided 400 mg of product. LC/MS: Retention time, 2.66 min; (M+H)=499.

후처리

  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 methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-82d14490e8494b3babc895eacd83bee1
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625889B2

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