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Lithium Hydroxide → HCID 68419598, compound

HRID 1765060
Notes
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Reaction equation

HRID 1765060 reaction equation
C([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([N:23]4[CH2:28][CH:27]([CH3:29])[N:26]([C:30](=[O:32])[CH3:31])[CH:25]([CH3:33])[CH2:24]4)[CH:18]=3)[N:13]=2)=[CH:7][CH:6]=1)C.C1COCC1.[OH-].[Li+]>CO.O>[C:30]([N:26]1[CH:25]([CH3:33])[CH2:24][N:23]([C:19]2[CH:18]=[C:17]([N:14]3[CH:15]=[N:16][C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:34])=[O:3])=[CH:6][CH:7]=4)=[N:13]3)[CH:22]=[CH:21][N:20]=2)[CH2:28][CH:27]1[CH3:29])(=[O:32])[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68421046HCID 68421046, compound

Product 1

HCID 68419598HCID 68419598, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962
Water
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of 16 g of 4-{1-[2-(4-Acetyl-3,5-dimethyl-piperazin-1-yl)-pyridin-4-yl]-1H-[1,2,4]triazol-3-ylamino}-benzoic acid ethyl ester (34.5 mMol, 1.00 equiv) in 200 mL of 1:1 MeOH:THF was added 5.75 g of lithium hydroxide (137 mMol, 4.00 equiv) in 100 mL of water. The solution was stirred at 60° C. for 12 hr and then the MeOH and THF were removed via rotary evaporation. The basic solution was neutralized by the addition of 68 mL of 2N HCl and the precipitate was isolated by filtration, yielding 12.5 g of 4-{1-[2-(4-Acetyl-3,5-dimethyl-piperazin-1-yl)-pyridin-4-yl]-1H-[1,2,4]triazol-3-ylamino}-benzoic acid (28.7 mMol, 83.5% yield) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) ∂ 10.215(1H, s), 9.48 (1H, s), 8.18 (1H, d), 7.91 (2h, d), 7.71 (2H, d), 7.49 (1H, s), 7.35 (1H, d), 4.38 (2H, m), 3.31 (4H, m), 2.10 (3H, s), 1.22 (6H, m) ppm. LC/MS: 2.02 min/436.30 (M+1)

Workup

  1. customthe MeOH and THF were removed via rotary evaporation
  2. additionThe basic solution was neutralized by the addition of 68 mL of 2N HCl
  3. customthe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-ca728cd71df246fab4be15c2ae17dea9
Source dataset
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07226920B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes