Trifluoroacetic acid → HCID 178482138, compound

HRID 1186276Notes

Reaction equation

[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([NH:25][C:26]([C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)=[NH:27])[CH:23]=3)[NH:18][CH:17]=2)[CH2:11]1)C(=O)OC(C)(C)C.FC(F)(F)C(O)=O.[NH4+].[OH-]>ClCCl>[CH3:1][NH:2][CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([NH:25][C:26]([C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)=[NH:27])[CH:23]=3)[NH:18][CH:17]=2)[CH2:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl methyl(3-(5-(thiophene-2-carboximidamido)-1H-indol-3-yl)cyclohexyl)carbamate (0.30 g, 0.66 mmol) was treated with 20% trifluoroacetic acid (TFA) solution (31 mL) in dichloromethane at 0° C. and the mixture left to stir for 2 h at 0° C. The solution then was neutralized with 10% NH4OH, the organic layer separated and evaporated. The crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:4) to give the title product as a yellow solid (0.22 g, quantitative). 1H-NMR (DMSO-d6) δ 1.28-1.61 (m, 4H), 1.84-2.01 (m, 2H), 2.08-2.11 (m, 1H), 2.27-2.35 (m, 1H), 2.58 (s, 3H), 2.86-2.94 (m, 1H), 3.08-3.25 (m, 1H), 7.10 (d, 1H, J=8.4 Hz), 7.28 (d, 1H, J=2.1 Hz), 7.39 (pseudo t, 1H, J=4.5 Hz), 7.52 (d, 1H, J=8.4 Hz), 7.65 (s, 1H), 8.12 (d, 1H, J=3.6 Hz), 8.16 (d, 1H, J=4.5 Hz), 8.58 (s, 2H, NH), 9.61 (s, 1H); ESI-MS (m/z, %) 353 (100), ESI-HRMS calc. for C20H25N4S 353.1794 found 353.1792.

Workup

waitthe mixture left
customthe organic layer separated
customevaporated
customThe crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:4)

Sources & evidence

ORD record: ord-5e3abd3e1bc94b6ab0158d1986f944e9
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673909B2

Reaction notes

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