2-Chloroethyl chloroformate → 8-[2-(2-Chloroethoxycarbonylamino)-6-methylbenzylamino]-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1954997Notes

Reaction equation

HRID 1954997 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][Cl:7])=[O:3].[NH2:8][C:9]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[N:15]([C:19]([CH3:23])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1>ClCCl>[Cl:7][CH2:6][CH2:5][O:4][C:2]([NH:8][C:9]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[N:15]([C:19]([CH3:23])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:3]

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 109896268-(2-Amino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine

Product 1

HCID 232941668-[2-(2-Chloroethoxycarbonylamino)-6-methylbenzylamino]-2,3-dimethylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloroethyl chloroformate (12.4 g, 81 mmol) dissolved in dichloromethane (40 ml) is added dropwise at RT, during the course of about 30 min, to a solution of 8-(2-amino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine (19.65 g, 70 mmol) in anhydrous dichloromethane (600 ml). The mixture is then stirred at RT for 16 h and then extracted with sodium hydrogen carbonate (4×200 ml). After extraction of the aqueous phases with dichloromethane (200 ml), the combined organic extracts are washed with water (2×200 ml), dried over magnesium sulfate and concentrated. The crude product which remains (33.9 g) is used directly for the further reaction in Example 1b.

Workup

  1. extractionextracted with sodium hydrogen carbonate (4×200 ml)
  2. extractionAfter extraction of the aqueous phases with dichloromethane (200 ml)
  3. washthe combined organic extracts are washed with water (2×200 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customis used directly for the further reaction in Example 1b

Sources & evidence

ORD record
ord-844e6ba03f644858bd057cba1045f1c1
Source dataset
uspto-grants-2000_09
Patent number
US06124313

Reaction notes

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