Sodium Bicarbonate → HCID 118521983, compound

HRID 1486752Notes

Reaction equation

HRID 1486752 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 118521983HCID 118521983, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9c2e5d3e675f45b9b7b6a07d468f933c
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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