1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → (E)-1-(2-chloroimidazo[1,2-a]pyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one

HRID 42260

Reaction equation

HRID 42260 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[C:11](=[O:13])[CH3:12].C(O[CH:19](OC(C)(C)C)[N:20]([CH3:22])[CH3:21])(C)(C)C>CN1CCCC1=O>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[C:11](=[O:13])/[CH:12]=[CH:19]/[N:20]([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 545941131-{2-Chloroimidazo[1,2-a]pyridin-3-yl}ethan-1-one

Product 1

HCID 59606857(E)-1-(2-chloroimidazo[1,2-a]pyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 100 mL round bottom flask, a solution of EXAMPLE 1C (4.25 g, 21.84 mmol), 1,1-di-tert-butoxy-N,N-dimethylmethanamine (28.8 mL, 120 mmol), and N-methyl-2-pyrrolidinone (15 mL) was heated at 85° C. for 2 hours. The reaction was concentrated under high vacuum on a rotavap at 60° C. The residual solid was triturated with 5 mL ether, filtered and dried to provide the title compound. MS (ES r) m/e 249.8 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated under high vacuum on a rotavap at 60° C
  2. customThe residual solid was triturated with 5 mL ether
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-72f551a871184881812c94a6e7bf6696
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Linked notes

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