2-Aminothiazole → HCID 178478541, compound

HRID 895384Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7](C1NC=CN=1)(C1NC=CN=1)=S.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH:27]([NH2:34])[CH2:28][N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.[C:35]1([CH:41]([NH2:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C>[ClH:19].[C:35]1([CH:41]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[NH:48][C:7]([NH:34][CH:27]([C:21]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:20]=2[Cl:19])[CH2:28][N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)=[N:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred solution of 2-aminothiazole (100 mg) in acetonitrile (3 mL) was added thiocarbonyl dimidazole (180 mg, 1.0 mmol). The mixture was allowed to stir at rt for 2 h and at 65° C. for 5 h, and then 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethylamine (250 mg, 1.0 mmol) was added. This was allowed to stir for 5 h at 65° C. The mixture was cooled to rt, and diphenylmethylamine was added, followed by TEA and mercuric chloride. The suspension was allowed to stir at rt for 3 h and filtered. The filtrate was concentrated and the residue purified by column chromatography (EtOAc, MeOH, NH4OH; 90:10:0.1) to give after conversion to HCT salt, the title compound as a yellow solid (100 mg). MS (ES): m/z 547 [M+H]+.

Workup

stirringto stir for 5 h at 65° C
temperatureThe mixture was cooled to rt
stirringto stir at rt for 3 h
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue purified by column chromatography (EtOAc, MeOH, NH4OH; 90:10:0.1)
customto give after conversion to HCT salt

Sources & evidence

ORD record: ord-d9f6a5190c164e32b2852318ce145482
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916813B2

Reaction notes

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