Hydrochloric Acid → HCID 136117295, compound

HRID 78647Notes

Reaction equation

HRID 78647 reaction equation
[Li+].[OH-].C([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[O:14][C:15]([C:18]2[C:23]([NH2:24])=[N:22][CH:21]=[C:20]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH:34]([CH3:36])[CH3:35])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[N:19]=2)=[N:16][N:17]=1)(=O)C.Cl>C1COCC1>[NH2:24][C:23]1[C:18]([C:15]2[O:14][C:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[OH:6])=[N:17][N:16]=2)=[N:19][C:20]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH:34]([CH3:36])[CH3:35])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:21][N:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 59472232HCID 59472232, compound

Product 1

HCID 136117295HCID 136117295, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (292.0 μL of 1 M, 0.2920 mmol) was added to a suspension of 2-(5-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl acetate (14 mg, 0.02920 mmol) in THF (5 mL) at ambient temperature. After 3 h, a further portion of LiOH (292.0 μL of 1 M, 0.2920 mmol) was added and the reaction continued to stir at room temperature for 1 h. 1M HCl was added dropwise until the reaction mixture was acidic and the resultant precipitate isolated by filtration. The solid residue was dissolved in a mixture of MeCN and water and lypholised to give the product as a green solid (5.1 mg, 38% yield); 1H NMR (400 MHz, DMSO) d 1.20 (d, 6H), 3.46 (m, 1H), 6.98-7.22 (m, 2H), 7.36-7.59 (m, 1H), 7.75-8.16 (m, 5H), 8.37 (d, 2H), 9.06 (s, 1H) and 10.43 (s, 1H) ppm; MS (ES+) 438.2

Sources & evidence

ORD record
ord-3326ebde13eb495cb90aff95ac1c3148
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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