Chloroacetyl chloride → HCID 21912251, compound

HRID 1813921Notes

Reaction equation

HRID 1813921 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].[Cl:25][CH2:26][C:27](Cl)=[O:28].C(N(CC)CC)C>C1COCC1>[Cl:25][CH2:26][C:27]([NH:24][C:8]1[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])=[N:10][C:11]([CH3:13])=[CH:12][C:7]=1[O:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:28]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 21912102HCID 21912102, compound

Product 1

HCID 21912251HCID 21912251, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-ethyl-propoxy)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3-diamine (103 mg, 0.315 mmol) in 4 ml of dry THF was added chloroacetyl chloride (36 mg, 0.315 mmol) and triethylamine (32 mg, 0.315 mmol) at 0° C. The mixture was warmed to room temperature and stirred at room temperature overnight. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 125 mg of brown residue. The brown residue was purified through silica gel column chromatography using 10% ethyl acetate in hexaneas eluentto give 59 mg of the title compounds as a tan solid, mp 79-82° C. 1H NMR (CDCl3) δ 8.15(brs,1H), 6.87(s,2H), 6.78(s,1H), 6.14(s,1H), 4.20(m,1H), 4.19(s,2H), 2.28(s,3H), 2.24(s,3H), 2.16(s,6H).

Workup

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

Sources & evidence

ORD record
ord-cca240c165d2438593e23889a6defc6f
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

Loading…