Hydrochloric Acid → HCID 178479272, compound

HRID 2225221Notes

Reaction equation

HRID 2225221 reaction equation
Cl.[F:2][C:3]([F:32])([F:31])[C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[C:7]([NH:9][CH2:10][C:11]([NH:13][C@@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1)=[O:12])=[O:8].Cl.C1COCC1.C(Cl)[Cl:40]>O1CCOCC1>[ClH:40].[NH2:20][C@@H:17]1[CH2:16][CH2:15][C@H:14]([NH:13][C:11](=[O:12])[CH2:10][NH:9][C:7](=[O:8])[C:6]2[CH:28]=[CH:29][CH:30]=[C:4]([C:3]([F:32])([F:31])[F:2])[CH:5]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21919333Tetrahydrofurane dichloromethaneHCID 178454051HCID 178454051, compound

Product 1

HCID 178479272HCID 178479272, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl cis-4-(2-(3-(trifluoromethyl)benzamido)acetamido)cyclohexylcarbamate hydrochloride salt (350 mg, 0.79 mmol, 1 eq) was dissolved in dioxane (5 mL) at room temperature then 4N HCl (1.97 mL, 7.9 mmol, 10 eq) was added. Stirred for 20 hours. The reaction was stripped 4 times from 1:1 THF/methylene chloride (20 mL) to give N-(2-(cis-4-amino-cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide hydrochloride (300 mg) as a white amorphous solid. MS found: (M+H)+=344.32.

Sources & evidence

ORD record
ord-29121de180444b2bbd4a11268a06b850
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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