Hydrochloric Acid → HCID 178523386, compound

HRID 245739Notes

Reaction equation

HRID 245739 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH2:9][NH2:10])=[N:5][CH:6]=[CH:7][N:8]=1.[CH2:11]([O:18][C:19]([NH:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29](O)=[O:30])[CH2:25][CH2:24]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N=C=NCCCN(C)C)C.Cl.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C:19](=[O:20])[NH:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29](=[O:30])[NH:10][CH2:9][C:4]2[C:3]([Cl:2])=[N:8][CH:7]=[CH:6][N:5]=2)[CH2:25][CH2:24]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 42614233(3-Chloropyrazin-2-yl)methanamine hydrochlorideHCID 178523389HCID 178523389, compound

Product 1

HCID 178523386HCID 178523386, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (3-chloropyrazin-2-yl)methanamine hydrochloride (5 g, 21.38 mmol), (trans)-4-((benzyloxycarbonylamino)methyl)cyclohexanecarboxylic acid (6.23 g, 21.38 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) hydrochloride (4.51 g, 23.52 mmol), 1-hydroxy-7-azabenzotriazole (1.455 g, 10.69 mmol), and triethyl amine (4.76 ml, 34.2 mmol) in dichloromethane (60 ml) was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by column chromatography (silica gel, dichloromethane with gradient 0.5 to 5% of methanol) to yield benzyl((trans)-4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl)methylcarbamate (8.79 g).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography (silica gel, dichloromethane with gradient 0.5 to 5% of methanol)

Sources & evidence

ORD record
ord-3480860f57ad409e85177266be1d3596
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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