Hydrochloric Acid → HCID 49806787, compound

HRID 2201724Notes

Reaction equation

HRID 2201724 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[C:30]([CH3:33])([CH3:32])[CH3:31])[C:5]([NH:7][C:8](=[S:26])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:12][CH:11]=1)=[O:6].[ClH:34]>CC(C)=O.C(OCC)C>[ClH:34].[Br:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[C:30]([CH3:33])([CH3:32])[CH3:31])[C:5]([NH:7][C:8](=[S:26])[NH:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[CH3:24])=[CH:14][CH:15]=1)=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 49806788HCID 49806788, compound

Product 1

HCID 49806787HCID 49806787, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

3-Bromo-4-tert-butyl-benzoyl chloride was prepared according to general procedure B from 3-bromo-4-tert-butyl-benzoic acid (500 mg) and used without further purification. 3-Bromo-4-tert-butyl-benzoyl chloride (295 mg, 1.07 mmol) was stirred in acetone (5 mL) and sodium thiocyanate (87 mg, 1.07 mmol) added to give a red-orange suspension which was stirred at room temperature for 16 h. A solution of 5-dimethylamino-pentanoic acid (4-amino-phenyl)-amide (4, prepared as described above) in acetone (5 mL) was added and the yellow suspension stirred for a further 16 h. The reaction mixture was diluted in dichloromethane and filtered to give a crude mixture which was purified by column chromatography eluting with methanol/dichloromethane (0% to 20%) to give 5-dimethylamino-pentanoic acid {4-[3-(3-bromo-4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide as a yellow solid. The hydrochloride salt was prepared by dissolving the amine in a minimal volume of acetone (1-2 mL) and adding 2 M hydrochloric acid in diethyl ether (200 μL). The resulting solid was filtered to give 5-dimethylamino-pentanoic acid {4-[3-(3-bromo-4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide hydrochloride (50 mg) as a yellow solid.

Workup

  1. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-796586e32d3e43dab86749e15becce5f
Source dataset
uspto-grants-2016_06
Patent number
US09365508B2

Reaction notes

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