Sodium Methoxide → HCID 71736261, compound

HRID 1481196Notes

Reaction equation

HRID 1481196 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])=[CH:10][CH:11]=2)[C:6]([OH:21])=[C:5]([C:22](OCCCC)=[O:23])[N:4]=1)#[N:2].OC(C(F)(F)F)=O.[NH2:36][CH2:37][C:38]([CH3:43])([CH3:42])[C:39]([OH:41])=[O:40].C[O-].[Na+]>CCO>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])=[CH:10][CH:11]=2)[C:6]([OH:21])=[C:5]([C:22]([NH:36][CH2:37][C:38]([CH3:43])([CH3:42])[C:39]([OH:41])=[O:40])=[O:23])[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 89813152HCID 89813152, compoundHCID 1317322153-Amino-2,2-dimethyl-propionic acid TFA salt

Product 1

HCID 71736261HCID 71736261, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Butyl 1-cyano-4-hydroxy-6-(o-tolyloxy)isoquinoline-3-carboxylate (11 mg, 0.03 mmol), 3-amino-2,2-dimethyl-propionic acid TFA salt (27.1 mg, 0.12 mmol) and NaOMe (12.3 mg, 0.23 mmol) in EtOH (3 mL) were heated at 150° C. in a microwave for 90 minutes. The solvent was removed in vacuo and the residue was dissolved in H2O (15 mL) and EtOAc (15 mL). To the stirred mixture was added 1 N hydrochloric acid until pH was 1. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-25% MeOH/CH2Cl2) to give the title compound in 7 mg. MS: (−) m/z 417.94 (M−1).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in H2O (15 mL)
  3. additionTo the stirred mixture was added 1 N hydrochloric acid until pH was 1
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted twice with EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (0-25% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-81f2d9d6b3ff48bc941525f709520483
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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