2-Pyrazinecarboxylic acid → HCID 43392686, compound

HRID 1624356Notes

Reaction equation

HRID 1624356 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[N:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[C:12](O)=[O:13].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.[Cl-].[Na+].O>[OH:5][CH2:4][CH2:3][CH2:2][NH:1][C:12]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][N:6]=1)=[O:13]

Participants

8

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 90863-Amino-1-propanolHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 43392686HCID 43392686, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-amino-1-propanol (1.20 mL, 15.7 mmol) in CH2Cl2 (80 mL) was added 2-pyrazinecarboxylic acid (1.99 g, 16.0 mmol), DIPEA (5.6 mL, 32.1 mmol), HOBT (2.61 g, 19.3 mmol) and EDC.HCl (3.70 g, 19.3 mmol). The solution was stirred at room temperature under nitrogen for 14.5 hours, then was diluted with brine (25 mL). The layers were separated and the aqueous solution was extracted with EtOAc (50 mL×3) and CHCl3 (50 mL×3). The combined organic solution was dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH/NH4OH, 19:1:0.1) gave the amide as a white solid (1.94 g, 10.7 mmol, 68%). 1H NMR (CDCl3) δ 1.83 (quint, 2H, J=5.9 Hz), 3.03 (br. s, 1H), 3.61-3.74 (m, 4H), 8.12 (br. s, 1H), 8.53 (dd, 1H, J=2.4, 1.5 Hz), 8.75 (d, 1H, J=2.4 Hz), 9.40 (d, 1H, J=1.5 Hz).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous solution was extracted with EtOAc (50 mL×3) and CHCl3 (50 mL×3)
  3. dry with materialThe combined organic solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography on silica (CH2Cl2/MeOH/NH4OH, 19:1:0.1)

Sources & evidence

ORD record
ord-4cb0e904eda8459b8f62e0fec06af2b2
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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