Triethylamine → HCID 67047767, compound

HRID 606931Notes

Reaction equation

HRID 606931 reaction equation
[CH2:1]([O:3][C:4]([Cl:6])=[O:5])[CH3:2].[C:7]1([C:13]#[C:14][C:15]2[CH:16]=[C:17]([CH2:21][NH2:22])[CH:18]=[N:19][CH:20]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[ClH:6].[CH2:1]([O:3][C:4](=[O:5])[NH:22][CH2:21][C:17]1[CH:18]=[N:19][CH:20]=[C:15]([C:14]#[C:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:16]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 67047975HCID 67047975, compound

Product 1

HCID 67047767HCID 67047767, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add ethylchloroformate (0.18 g, 1.63 mmol) to a solution of C-(5-phenylethynyl-pyridin -3-yl)-methylamine, (prepared as described in EXAMPLE 167), (0.20 g, 0.82 mmol) and triethylamine (0.33 g, 3.27 mmol) in dichloromethane (1.6 mL). Stir overnight, and dilute with dichloromethane. Wash with an aqueous saturated solution of sodium bicarbonate, dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes, to give the free base of the title compound. Dissolve the free base in diethyl ether and add a 1 M solution of hydrogen chloride (1.1 eq.) in diethyl ether. Stir for 2 h and collect the precipitated solid by filtration to give the title compound (0.18 g, 70%).

Workup

  1. washWash with an aqueous saturated solution of sodium bicarbonate
  2. dry with materialdry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify by silica gel chromatography
  6. washeluting with 50:50 ethyl acetate

Sources & evidence

ORD record
ord-4be3e68847054176b07aba4c309b9aa6
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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