HCID 68927965, compound → HCID 11503382, compound

HRID 1785951Notes

Reaction equation

HRID 1785951 reaction equation
[C:1]([N:4]([C@H:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]([C:31](=[O:40])[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[C@@H:23]([CH3:41])[CH2:22]1)[C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2C(OC(C)(C)C)=O)(=[O:3])[CH3:2]>Cl.O1CCOCC1>[NH:9]1[C:10]2[C:6](=[C:5]([N:4]([C@H:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([C:31](=[O:40])[C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C@@H:23]([CH3:41])[CH2:22]3)[C:1](=[O:3])[CH3:2])[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

4

Reactant 1

HCID 68927965HCID 68927965, compound

Product 1

HCID 11503382HCID 11503382, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-{acetyl[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-1H-indole-1-carboxylate (0.035 g, 0.068 mmol) was stirred in 4 N HCl in dioxane (1 mL) for 24 h and then evaporated to dryness. The residue was dissolved in ethyl acetate, washed with 1N NaOH, water, brine, dried over sodium sulphate and evaporated to dryness to give the crude product (0.023 g). The crude was cleaned by silica gel chromatography to give clean N-1H-indol-4-yl-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (0.008 g, 28%).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1N NaOH, water, brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness
  6. customto give the crude product (0.023 g)

Sources & evidence

ORD record
ord-b278750930c742c0af53f041ab8367ae
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…