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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
ノート
印刷プレビュー

反応式

HRID 1486752 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c2e5d3e675f45b9b7b6a07d468f933c
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09428456B2

反応ノート

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