Acetic Acid → Ethyl 4-[({3-[(tert-butoxycarbonyl)amino]pyridin-4-yl}methyl)amino]piperidine-1-carboxylate

HRID 501097

반응식

HRID 501097 반응식
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:2].[Na+].C(O)(=O)C.[C:19]([N:26]1C=CC(C=O)=[C:28]([NH2:34])[CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[NH2:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:38][CH2:37]1.Cl[CH:48](Cl)[CH3:49]>>[C:22]([O:21][C:19]([NH:26][C:27]1[CH:28]=[N:34][CH:1]=[CH:2][C:48]=1[CH2:49][NH:35][CH:36]1[CH2:37][CH2:38][N:39]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:40][CH2:41]1)=[O:20])([CH3:23])([CH3:24])[CH3:25]

참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 70700445N-Boc-3-amino-4-pyridine carboxaldehyde

생성물 1

HCID 22293284Ethyl 4-[({3-[(tert-butoxycarbonyl)amino]pyridin-4-yl}methyl)amino]piperidine-1-carboxylate

실험 절차

Sodium triacetoxyborohydride (0.57 g, 2.70 mmol) and acetic acid (0.41, 6.75 mmol) were added to a solution of N-Boc-3-amino-4-pyridine carboxaldehyde (0.50 g, 2.25 mmol) and ethyl 4-aminopiperidine-1-carboxylate (0.47 g, 2.70 mmol) in dichloroethane (5 mL) at room temperature. The reaction was stirred overnight, and quenched with saturated aqueous sodium bicarbonate. This was separated, extracted with ethyl acetate and the combined organics were dried over sodium sulfate. The solution was filtered and evaporated to give the crude product. This was purified by chromatography (silica gel, 1 to 12% methanol in methylene chloride gradient elution), which gave the title compound (0.47 g). MS 379.3.

후처리

  1. customquenched with saturated aqueous sodium bicarbonate
  2. customThis was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated
  7. customto give the crude product
  8. customThis was purified by chromatography (silica gel, 1 to 12% methanol in methylene chloride gradient elution), which

출처 및 근거

ORD 기록
ord-7597ef02e405429a8d0c1fafb8776021
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772224B2

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