Trifluoroacetic acid → HCID 86622757, compound

HRID 1020259Notes

Reaction equation

C([O:5][C:6](=[O:29])[CH2:7][N:8]([CH2:10][C:11]1[N:12]=[C:13]([NH:16][C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)=[O:18])[S:14][CH:15]=1)[CH3:9])(C)(C)C.FC(F)(F)C(O)=O>>[ClH:27].[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[Cl:27])[CH2:20][NH:19][C:17](=[O:18])[NH:16][C:13]1[S:14][CH:15]=[C:11]([CH2:10][N:8]([CH2:7][C:6]([OH:29])=[O:5])[CH3:9])[N:12]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86622758HCID 86622758, compound

Product 1

HCID 86622757HCID 86622757, compound

Procedure

({2-[3-(3,4-Dichloro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amino)-acetic acid tert-butyl ester (Example 109) was treated with trifluoroacetic acid overnight. The TFA was removed by evaporation the residue was triturated with 2N HCl in diethyl ether to afford the title compound. 1H-NMR (300 MHz, CD3OD): δ 7.48 (d, 2H), 7.25 (d, 2H), 7.18 (s, 1H), 4.40 (s, 2H), 4.33 (s, 2H), 3.89 (s, 2H), 2.91 (s, 3H). M/z (pos. ESI)=402 (M+H).

Workup

customThe TFA was removed by evaporation the residue
customwas triturated with 2N HCl in diethyl ether

Sources & evidence

ORD record: ord-bf299ea5431f49678a47d7f0e375b399
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716320B2

Reaction notes

Loading…