HCID 57815280, compound → HCID 24864371, compound

HRID 385642Notes

Reaction equation

HRID 385642 reaction equation
[O:1]1[C:11]2[CH:10]=[C:9]([CH2:12][N:13]([CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][N:29]4[C:34](=[O:35])[CH:33]=[N:32][C:31]5[N:36]=[CH:37][C:38]([O:40][CH3:41])=[CH:39][C:30]4=5)[CH2:23][CH2:22]3)C(=O)OC(C)(C)C)[N:8]=[CH:7][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1>ClCCl.FC(F)(F)C(O)=O>[O:1]1[C:11]2[CH:10]=[C:9]([CH2:12][NH:13][CH:21]3[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][N:29]4[C:34](=[O:35])[CH:33]=[N:32][C:31]5[N:36]=[CH:37][C:38]([O:40][CH3:41])=[CH:39][C:30]4=5)[CH2:25][CH2:26]3)[N:8]=[CH:7][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57815280HCID 57815280, compound

Product 1

HCID 24864371HCID 24864371, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 87 mg of tert-butyl (3,4-dihydro-2H-(1,4)dioxepino(2,3-c)pyridin-8-ylmethyl)(1-(2-(7-methoxy-2-oxopyrido(2,3-b)pyrazin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate in 2 mL of dichloromethane, 2 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and chloroform and water were added thereto. The aqueous layer was separated and adjusted to pH 13.1 with a 20% aqueous sodium hydroxide solution. Chloroform was added thereto, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 54 mg of 1-(2-(4-((3,4-dihydro-2H-(1,4)dioxepino(2,3-c)pyridin-8-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxypyrido(2,3-b)pyrazin-2(1H)-one as a yellowish brown oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and chloroform and water
  2. additionwere added
  3. customThe aqueous layer was separated
  4. additionChloroform was added
  5. customthe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washthe resultant solution was washed sequentially with water
  8. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2804446d76924fae960f8085b96ab8d3
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

Loading…