Hydrochloric Acid → HCID 56932992, compound

HRID 1972642Notes

Reaction equation

[C:1]([CH:4]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH2:8][CH2:7][N:6]([S:26]([C:29]2[S:33][C:32]([NH:34]C(=O)C)=[N:31][N:30]=2)(=[O:28])=[O:27])[CH2:5]1)#[C:2][CH3:3].Cl.O1CCOCC1>CO>[NH2:34][C:32]1[S:33][C:29]([S:26]([N:6]2[CH2:7][CH2:8][N:9]([C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:25])([C:17]([F:19])([F:20])[F:18])[C:21]([F:23])([F:24])[F:22])=[CH:14][CH:15]=3)[CH:4]([C:1]#[C:2][CH3:3])[CH2:5]2)(=[O:27])=[O:28])=[N:30][N:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 20-mL microwave vial was charged with N-(5-((3-(1-propyn-1-yl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-piperazinyl)sulfonyl)-1,3,4-thiadiazol-2-yl)acetamide (370 mg, 0.647 mmol), MeOH (2 mL), 1N aq. HCl (3 mL, 3.00 mmol) and 4N HCl in dioxane (3 mL, 12.00 mmol). The reaction vessel was sealed and the mixture heated to 100° C. for 4 h. The reaction was concentrated onto silica and purified via column chromatography on silica gel (0 to 10% MeOH in CH2Cl2) to give 2-(4-(4-((5-amino-1,3,4-thiadiazol-2-yl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (160 mg) as a mixture of two isomers.

Workup

customThe reaction vessel was sealed
concentrationThe reaction was concentrated onto silica
custompurified via column chromatography on silica gel (0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-19537745148f4f0d966635525a104ddb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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