Lithium Hydroxide → HCID 24936362, compound

HRID 76068Notes

Reaction equation

HRID 76068 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][N:25]=4)=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[Li+].[OH-]>C1COCC1.CO>[CH3:31][S:30][C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([C:14]3[CH:15]=[CH:16][C:11]([CH:8]4[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:32])=[O:2])[CH2:10][CH2:9]4)=[CH:12][CH:13]=3)=[N:18][CH:19]=2)=[N:25][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66616190(4-{4-[5-(5-Methylsulfanyl-pyridin-2-ylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 24936362HCID 24936362, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The crude (4-{4-[5-(5-Methylsulfanyl-pyridin-2-ylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester was dissolved in THF/MeOH (4:1, 2.5 mL) and to it was added aqueous LiOH (4M, 0.5 mL). The mixture was stirred at room temperature for 18 hours, then was immediately purified via reverse-phase HPLC to yield the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08-1.20 (m, 2H) 1.44-1.57 (m, 2H) 1.84 (m, 5H) 2.16 (d, J=6.82 Hz, 2H) 2.50 (m, 1H) 6.91 (d, J=8.59 Hz, 1H) 7.36 (d, J=8.34 Hz, 2H) 7.70 (dd, J=8.59, 2.53 Hz, 1H) 7.91 (d, J=8.34 Hz, 2H) 7.95 (d, J=8.84 Hz, 1H) 8.21 (d, J=2.27 Hz, 1H) 8.33 (dd, J=9.09, 2.53 Hz, 1H) 8.98 (br. s., 1H) 9.64 (br. s., 1H); MS (M+H)+434.2.

Workup

  1. customwas immediately purified via reverse-phase HPLC

Sources & evidence

ORD record
ord-56518ac625ce463293e00cc7cf3ac7b5
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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