2-Pyrazinecarboxylic acid → HCID 43392686, compound

HRID 899707Notes

Reaction equation

HRID 899707 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-82d27f89f2e74b1193c09ca07394ad66
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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