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Sodium Dithionite → (R)-tert-Butyl(1-(2-(1-ethyl-1H-pyrrolo[2,3-c]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate

HRID 2275010
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HRID 2275010 반응식
S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:9]([O:13][C:14](=[O:35])[NH:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22](=[O:34])[C:23]2[CH:28]=[CH:27][C:26]([NH:29][CH3:30])=[C:25]([N+:31]([O-])=O)[CH:24]=2)[CH2:17]1)([CH3:12])([CH3:11])[CH3:10].[CH2:36]([N:38]1[C:42]2=[CH:43][N:44]=[CH:45][CH:46]=[C:41]2[CH:40]=[C:39]1[CH:47]=O)[CH3:37]>O.C(O)C.C(Cl)Cl.S([O-])([O-])(=O)=O.[Na+].[Na+]>[C:9]([O:13][C:14](=[O:35])[NH:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([C:23]2[CH:28]=[CH:27][C:26]3[N:29]([CH3:30])[C:47]([C:39]4[N:38]([CH2:36][CH3:37])[C:42]5=[CH:43][N:44]=[CH:45][CH:46]=[C:41]5[CH:40]=4)=[N:31][C:25]=3[CH:24]=2)=[O:34])[CH2:17]1)([CH3:12])([CH3:10])[CH3:11]
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참가 물질

8

반응물 3

HCID 24489Sodium DithioniteHCID 863401791,1-Dimethylethyl ((3R)-1-{[4-(methylamino)-3-nitrophenyl]carbonyl}-3-piperidinyl)carbamateHCID 900281891-ethyl-1H-pyrrolo[2,3-c]pyridine-2-carbaldehyde

생성물 1

HCID 118178620(R)-tert-Butyl(1-(2-(1-ethyl-1H-pyrrolo[2,3-c]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate수율 31.7%

시약·촉매·용매 4

HCID 702
Ethanol
용매
HCID 962Water용매
HCID 6344Dichloromethane용매
HCID 24436Sodium Sulfate용매

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온도
100 °C

실험 절차

Sodium hydrosulfite (162 mg, 0.793 mmol) dissolved in water (1 mL) was added to a solution of (R)-tert-butyl(1-(4-(methylamino)-3-nitrobenzoyl)piperidin-3-yl)carbamate (100 mg, 0.264 mmol) and 1-ethyl-1H-pyrrolo[2,3-c]pyridine-2-carbaldehyde (46.0 mg, 0.264 mmol) in ethanol (2 mL) at RT under nitrogen. The reaction mixture was heated to 100° C. in a microwave for 5 h. The reaction mixture was diluted with DCM (20 mL), sodium sulfate was added and the resultant suspension filtered and concentrated in vacuo to yield the crude product. This was purified by Biotage SP4 on a SNAP 10 g silica cartridge using a gradient of 0% (20% MeOH/DCM)/DCM→50% (20% MeOH/DCM)/DCM. Appropriate fractions were combined and evaporated under vacuum to give the title compound (42 mg)

후처리

  1. additionwas added
  2. filtrationthe resultant suspension filtered
  3. concentrationconcentrated in vacuo
  4. customto yield the crude product
  5. customThis was purified by Biotage SP4 on a SNAP 10 g silica cartridge
  6. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-ad8b3480fd564ca0bb629c821f72d67f
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09127003B2

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