1,4-Oxazepane → HCID 86687039, compound

HRID 1402176Notes

Reaction equation

HRID 1402176 reaction equation
Cl[C:2]1[N:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[CH2:12]1[CH2:18][O:17][CH2:16][CH2:15][NH:14][CH2:13]1>CN1C(=O)CCC1>[F:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([N:14]3[CH2:13][CH2:12][CH2:18][O:17][CH2:16][CH2:15]3)=[N:3][N:4]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 218732751,4-OxazepaneHCID 552675403-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 86687039HCID 86687039, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of Intermediate 24b (429 mg, 2.50 mmol) and homomorpholine (939 mg, 9.30 mmol) in NMP (10 mL) was heated in the microwave at 170° C. for 10 h. The cooled mixture was applied to an SCX-2 cartridge (70 g), washing with methanol then eluting basic components with 0.4-2 M NH3 in MeOH. Product containing fractions were combined and concentrated in vacuo. The residue was purified by FCC, using 0-12% [2M NH3 in MeOH] in DCM, to give impure product. Further purified by FCC, using 0-12% MeOH in EtOAc gave the title compound as a pale brown gum (147 mg, 25%). LCMS (Method 3): Rt 2.11 min, m/z 237 [MH+].

Workup

  1. washwashing with methanol
  2. washthen eluting basic components with 0.4-2 M NH3 in MeOH
  3. additionProduct containing fractions
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by FCC
  6. customto give impure product
  7. customFurther purified by FCC

Sources & evidence

ORD record
ord-3bc054b1643b42cdabcd27d80c71f3fe
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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