Sodium Hydroxide → HCID 178424091, compound

HRID 1497931Notes

Reaction equation

HRID 1497931 reaction equation
[F:1][C:2]1([F:32])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:31])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[CH:26][C:27]([C:29]#[CH:30])=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1.C(OC[N:41]=[N+:42]=[N-:43])(=O)C(C)(C)C.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[OH-].[Na+]>CC(O)(C)C.O.CO.[O-]S([O-])(=O)=O.[Cu+2]>[F:32][C:2]1([F:1])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:31])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[CH:26][C:27]([C:29]6[N:41]=[N:42][NH:43][CH:30]=6)=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 11521126Azidomethyl 2,2-dimethylpropanoateHCID 23667548Sodium AscorbateHCID 86677526HCID 86677526, compound

Product 1

HCID 178424091HCID 178424091, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 887MethanolSolventHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

A mixture of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-ethynylimidazo[1,2-a]pyridine-3-carboxamide (53) (10 mg, 0.023 mmol), azidomethyl pivalate (3.64 mg, 0.023 mmol), CuSO4(2 μL of 0.5M aqueous solution, 0.001 mmol) and sodium ascorbate (1.4 mg, 0.007 mmol) in tBuOH/H2O (1 mL, 2:1) was stirred at room temperature overnight. Then the reaction mixture was diluted and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated to afford a residue which was dissolved in MeOH (1 mL). Aqueous NaOH (0.6 mL, 1N) was added and the reaction mixture was stirred for 30 minutes. The above mixture was purified by HPLC to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-(1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (F65). MS m/z 477.1 (M+1)+.

Workup

  1. additionThen the reaction mixture was diluted
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a residue which
  7. stirringthe reaction mixture was stirred for 30 minutes
  8. customThe above mixture was purified by HPLC

Sources & evidence

ORD record
ord-279d8130cf9a4942b1cb179fe5b8166a
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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