Hydrochloric Acid → HCID 178512479, compound

HRID 1246475Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:13][CH:14]=2)=[CH:4][CH:3]=1.[N:26]#[C:27][NH2:28].Cl>C(OCC)(=O)C.C(O)C>[NH2:28][C:27]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:25])[S:13][CH:14]=2)=[CH:4][CH:3]=1)=[NH:26]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of benzyl 4-[2-(4-aminophenyl)ethyl]-1,3-thiazol-2-ylcarbamate (25 mg), cyanamide (6.0 mg), 4N hydrogen chloride in ethyl acetate (0.018 ml) and ethanol (1 ml) was stirred at 100° C. for 72 hours. The reaction mixture was concentrated in vacuo. To the residue was added ethyl acetate (5 ml) and saturated aqueous sodium hydrogen bicarbonate (5 ml). The precipitated solid was filtered and washed with ethylacetate and water to give benzyl 4-[2-(4-{[amino(imino)methyl]amino}phenyl)ethyl]-1,3-thiazol-2-carbamate (15 mg).

Workup

concentrationThe reaction mixture was concentrated in vacuo
additionTo the residue was added ethyl acetate (5 ml) and saturated aqueous sodium hydrogen bicarbonate (5 ml)
filtrationThe precipitated solid was filtered
washwashed with ethylacetate and water

Sources & evidence

ORD record: ord-cacc4a084ca246d8901a93095a6350d5
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125901B2

Reaction notes

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