Lithium hydroxide, monohydrate → HCID 67325696, compound

HRID 709300Notes

Reaction equation

HRID 709300 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][C:12]([CH2:15][NH:16][C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=2[CH3:27])[C:20]([O:22]C)=[O:21])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.CO.O>[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][C:12]([CH2:15][NH:16][C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=2[CH3:27])[C:20]([OH:22])=[O:21])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67325229HCID 67325229, compound

Product 1

HCID 67325696HCID 67325696, compoundYield 79.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-((5-(tert-butoxycarbonylamino)pyrazin-2-yl)methylamino)-4-methylbenzoate (600 mg, 1.61 mmol) in THF (2 mL) and MeOH (2 mL) was added LiOH.H2O (338 mg, 8.06 mmol) in water (2 mL). The reaction mixture was stirred for overnight at room temperature. The organic solvent was removed under reduced pressure and water (4 mL) was added to the reaction mixture. To a reaction mixture was added 1N HCl solution to produce solid. The solid product was filtered and dried with nitrogen gas flow. The title product (460 mg, 79% yield) was used next reaction without further purification. MS m/z: 359 [M+1].

Workup

  1. customThe organic solvent was removed under reduced pressure and water (4 mL)
  2. additionwas added to the reaction mixture
  3. additionTo a reaction mixture was added 1N HCl solution
  4. customto produce solid
  5. filtrationThe solid product was filtered
  6. customdried with nitrogen gas flow

Sources & evidence

ORD record
ord-0082530db47b47ab8cd368305944594e
Source dataset
uspto-grants-2015_11
Patent number
US09180127B2

Reaction notes

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