Water → HCID 58447008, compound

HRID 1045755Notes

Reaction equation

HRID 1045755 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[N:16]([CH:25]=[C:26]([C:28]([O:30]CC)=[O:29])[N:27]=3)[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[N:16]([CH:25]=[C:26]([C:28]([OH:30])=[O:29])[N:27]=3)[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58447048HCID 58447048, compound

Product 1

HCID 58447008HCID 58447008, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A 100 mL round bottom flask was charged with ethyl 8-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-(thiophen-2-yl)imidazo[1,2-a]pyrazine-2-carboxylate (prepared as described in Example 61 steps 1-5, 0.80 g, 1.75 mmol), LiOH (0.22 g, 5.25 mmol), water (2 mL) and THF (30 mL). The mixture was stirred at 25° C. for 16 h. Reaction progress was monitored by LC-MS. Work-up: the solvent was evaporated. The residue was acidified with 2 N HCl. The precipitate was collected by filtration and dried, to afford 0.57 g (76%) of the product. MS m/z: 428 (M−H+).

Workup

  1. customReaction progress
  2. customthe solvent was evaporated
  3. filtrationThe precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-ceced5d0ce8f42c395cee1e251d2abd9
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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