HCID 66692781, compound → HCID 178499437, compound

HRID 406291Notes

Reaction equation

HRID 406291 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[C:9]([C:15]([O:17]C)=O)=[CH:8][CH:7]=1.[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[O:27][C@H:28]1[CH2:31][C@H:30]([NH2:32])[CH2:29]1.C1(C2CCCCCCCCC=2)CCCCCCNNN=1>C1COCC1.C(Cl)Cl>[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[O:27][C@H:28]1[CH2:29][C@H:30]([NH:32][C:15]([C:9]2[C:10]3[N:11]([CH:12]=[CH:13][N:14]=3)[C:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=2)=[O:17])[CH2:31]1

Participants

6

Reactant 3

HCID 66692781HCID 66692781, compoundHCID 86710849Methyl 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxylateHCID 178511742HCID 178511742, compound

Product 1

HCID 178499437HCID 178499437, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of methyl 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxylate (438 mg, 1.75 mmol), trans-3-[(2,3-dichlorophenyl)oxy]cyclobutanamine (463 mg, 1.995 mmol) and triazabicyclodecene (75 mg, 0.539 mmol) in THF (0.5 mL) was stirred in a sealed tube at room temperature for 18 hours. The reaction mixture was then transferred to a round bottomed flask using DCM as solvent and evaporated in vacuo to give yellow/brown gum which solidified (1.5 g). This material was dissolved in DCM and purified on silica (70 g) using a 0-100% ethyl acetate-cyclohexane gradient over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound as yellow crystals (601 mg).

Workup

  1. customThe reaction mixture was then transferred to a round bottomed flask
  2. customevaporated in vacuo
  3. customto give yellow/brown gum which
  4. custompurified on silica (70 g)
  5. customover 40 min
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a549cc80c4ae4ae6bb9b0f27fce1d21a
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

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