HCID 70975558, compound → HCID 53312240, compound

HRID 1190820Notes

Reaction equation

HRID 1190820 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]3[N:21](CC4C=CC(OC)=CC=4OC)[C:22](=[O:33])[N:23]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]#[N:32])[C:15]=23)[CH2:9]1)(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]3[NH:21][C:22](=[O:33])[N:23]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]#[N:32])[C:15]=23)[CH2:9]1

Participants

4

Reactant 1

HCID 70975558HCID 70975558, compound

Product 1

HCID 53312240HCID 53312240, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

1.24 g (R)-1-[1-(2-cyanobenzyl)-3-(2,4-dimethoxybenzyl)-5-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]piperidine-3-carbamic acid tert-butyl ester (2.02 mmol) was dissolved in 8 mL anisole, to which 1.5 mL trifluoroacetic acid was added, and reacted for 24 h at 90° C. The reaction solution was evaporated to dryness. The residue was dissolved in a small amount of water, and washed with ethyl acetate. The aqueous phase was adjusted to basic with saturated sodium carbonate solution, and extracted with dichloromethane for five times. The dichloromethane phase was combined, dried and evaporated to dryness to afford 0.4 g titled product with a yield of 54.5%.

Workup

  1. additionwas added
  2. customreacted for 24 h at 90° C
  3. customThe reaction solution was evaporated to dryness
  4. dissolutionThe residue was dissolved in a small amount of water
  5. washwashed with ethyl acetate
  6. extractionextracted with dichloromethane for five times
  7. customdried
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-5e4139829fb54a1fa348961d047bbf9b
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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