Lithium Hydroxide → HCID 68419598, compound

HRID 1817116Notes

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]

Participants

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 (2 h, 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

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

Sources & evidence

ORD record: ord-0609f7f56aa04e988e4d9e34d573a134
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598245B2

Reaction notes

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