Triphosgene → HCID 18386643, compound

HRID 2298433Notes

Reaction equation

HRID 2298433 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([O:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])=[N:5][C:6]([CH3:15])=[CH:7][C:8]=1[NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12].Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH2:13]([CH:10]([N:9]1[C:8]2[CH:7]=[C:6]([CH3:15])[N:5]=[C:4]([O:16][C:17]3[C:18]([CH3:25])=[CH:19][C:20]([CH3:24])=[CH:21][C:22]=3[CH3:23])[C:3]=2[CH2:2][NH:1][C:27]1=[O:29])[CH2:11][CH3:12])[CH3:14]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 21912181HCID 21912181, compound

Product 1

HCID 18386643HCID 18386643, compoundYield 310.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [3-Aminomethyl-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-(1-ethyl-propyl)-amine (100 mg, 0.292 mmol) in dry THF was added triphosgene (34 mg, 0.114 mmol) at 0° C. The reaction mixture was allowed to gradually warm to rt and stir for 2 h. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to dryness to give 130 mg of a clear oil. The solid was purified through silica gel column chromatography using 10% EtOAc in hexane as eluent to give 89 mg (82.4%)of the title compound as a white crystalline solid, mp 197-199° C. 1H NMR (CDCl3) d 6.86(s,2H), 6.44(s,1H), 5.14(brs,1H), 4.49(s,2H), 4.20(m,1H), 2.28(s,3H), 2.22(s,3H), 2.04(s,6H), 1.67(m,4H), 0.94(t,6H)ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9078145f926f49e6b37acead11f5505d
Source dataset
uspto-grants-2002_12
Patent number
US06492520B1

Reaction notes

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