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Sodium Bicarbonate → {6-[3-(4-tert-Butylcarbamoyl-piperidin-1-ylmethyl)-phenylcarbamoyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

HRID 1486752
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HRID 1486752 반응식
[CH3:1][C:2]([CH3:17])([O:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([OH:16])=O)=[N:12][CH:13]=1)=[O:6])[CH3:3].[C:18]([NH:22][C:23]([CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([NH2:38])[CH:33]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CCN=C=NCCCN(C)C.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:2]([O:4][C:5](=[O:6])[NH:7][C:8]1[CH:13]=[N:12][C:11]([C:14](=[O:16])[NH:38][C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([CH2:31][N:28]3[CH2:27][CH2:26][CH:25]([C:23](=[O:24])[NH:22][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:30][CH2:29]3)[CH:33]=2)=[CH:10][CH:9]=1)([CH3:1])([CH3:3])[CH3:17]
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참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 288755215-{[(Tert-butoxy)carbonyl]amino}pyridine-2-carboxylic acidHCID 867065251-(3-Amino-benzyl)-piperidine-4-carboxylic acid tert-butylamide

생성물 1

HCID 118521983{6-[3-(4-tert-Butylcarbamoyl-piperidin-1-ylmethyl)-phenylcarbamoyl]-pyridin-3-yl}-carbamic acid tert-butyl ester
수율 58%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 5-[[(1,1-dimethylethoxy)carbonyl]amino]-2-pyridinecarboxylic acid (1 g, 4.11 mmol) in DCM (30 mL) is treated successively with 1-(3-amino-benzyl)-piperidine-4-carboxylic acid tert-butylamide (1.309 g, 4.525 mmol), EDC-HCl (1.577 g, 8.227 mmol), DMAP (75 mg, 0.62 mmol). The RM is stirred at RT for 18 h. DCM (10 mL) and aq. sat. NaHCO3 solution (30 mL) are added and the organic phase is extracted twice with DCM (2×20 mL). The combined organic layers are dried over MgSO4, filtered and evaporated. The residue is purified by flash chromatography on silica gel using a gradient of DCM/MeOH from DCM to DCM/MeOH 9:1. After concentration of the product containing fractions, the title compound (1.21 g, 58%) is obtained as a beige powder LC-MS A: tR=0.75 min; [M+H]+=510.23.

후처리

  1. extractionthe organic phase is extracted twice with DCM (2×20 mL)
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by flash chromatography on silica gel using a gradient of DCM/MeOH from DCM to DCM/MeOH 9:1
  6. additionAfter concentration of the product containing fractions

출처 및 근거

ORD 기록
ord-9c2e5d3e675f45b9b7b6a07d468f933c
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09428456B2

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