Formic Acid → HCID 58902031, compound

HRID 448986Notes

Reaction equation

HRID 448986 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:5]([CH2:10][NH2:11])=[N:6][CH:7]=[CH:8][N:9]=1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.[CH:33](O)=[O:34]>CN(C=O)C>[Cl:3][C:4]1[C:5]([CH2:10][NH:11][CH:33]=[O:34])=[N:6][CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42609650(3-Chloropyrazin-2-yl)methanamine dihydrochloride

Product 1

HCID 58902031HCID 58902031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of C-(3-chloro-pyrazin-2-yl)-methylamine bis-hydrochloride (6.0 g, 0.027 mol) in DMF (50 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (7.9 g, 0.041 mol), diisopropyl ethylamine (24.2 mL, 0.139 mol), hydrate (400.0 mg, 0.003 mol) and formic acid (1.57 mL, 0.041 mol). The reaction was left to stir at rt for 16 h under an atmosphere of nitrogen. The solvent was then removed under reduced pressure and the residue was purified by chromatography (5% DCM in hexane. 1H NMR (400 MHz, CD3OD) δ ppm 4.72 (s, 2H), 8.26 (s, 1H), 8.39 (d, J=1.77 Hz, 1H), 8.57 (d, J=2.53 Hz, 1H). MS (ES+): m/z 172.11, 174.09 [MH+]; HPLC: tR=1.57 min (OpenLynx, polar—7 min).

Workup

  1. waitThe reaction was left
  2. customThe solvent was then removed under reduced pressure
  3. customthe residue was purified by chromatography (5% DCM in hexane
  4. customHPLC: tR=1.57 min (OpenLynx, polar—7 min)

Sources & evidence

ORD record
ord-3db31aa0225b469daec2bf2cb902f567
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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