Hydrochloric Acid → HCID 14499840, compound

HRID 2073805Notes

Reaction equation

HRID 2073805 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23]C(OC(C)(C)C)=O)[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16][C:17]#[CH:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.Cl>C(O)C>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16][C:17]#[CH:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14499828HCID 14499828, compound

Product 1

HCID 14499840HCID 14499840, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 8-(2-methyl-6-t-butoxycarbonylaminobenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (8.42 g) in ethanol (67 ml) was added dropwise 23%-ethanolic hydrogen chloride (26 g) at room temperature and the mixture was stirred for 6 hours. The resultant solid was siolated by filtration and dispersed into a mixture of an aqueous solution of sodium bicarbonate and chloroform. The chloroform layer was separated and washed with water and dried over magnesium sulfate. Following filtration, the solvent was removed under reduced pressure to give 8-(2-methyl-6-aminobenzylamino)-3-(2-propynyl)-2methylimidazo[1,2-a]pyridine (4.08 g). The crude crystzals (0.5 g) were recrystallized from a mixture of chloroform and n-hexane to give 0.46 g of pure crystals.

Workup

  1. filtrationThe resultant solid was siolated by filtration
  2. additiondispersed into a mixture of an aqueous solution of sodium bicarbonate and chloroform
  3. customThe chloroform layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltration
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6e0f277b4fb647fb8538026a8776a7f9
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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