Trifluoroacetic acid → HCID 178482138, compound

HRID 1186281Notes

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.C(O)(C(F)(F)F)=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 (0.60 g, 0.13 mmol) was treated with 20% TFA solution (31 mL) in dichloromethane at 0° C. and the mixture left to stir for 2 hours at 0° C. The solution then was neutralized with 10% NH4OH, the organic layer separated and evaporated. The crude product was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:4) to give the final product as a yellow solid (0.45 g, quantitative). 1H-NMR (DMSO-d6) δ 1.51-1.60 (m, 3H), 1.69-1.77 (m, 3H), 1.83-1.91 (m, 1H), 1.96-2.07 (m, 1H), 2.40 (s, 3H), 3.24-3.51 (m, 3H), 6.20 (brs, 2H, NH), 6.63 (d, 1H, J=10.2 Hz), 7.02 (d, 2H, J=10.4 Hz), 7.09 (dd, 1H, J=3.6, 4.8 Hz), 7.58 (d, 1H, J=5.1 Hz), 7.71 (d, 1H, J=3.3 Hz), 10.59 (s, 1H, NH); ESI-MS (m/z, %) 353 (MH+, 80), 322 (100), ESI-HRMS (MH+) calc. for C20H25N4S (MH+), calculated: 353.1794. found: 353.1812.

Workup

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

Sources & evidence

ORD record: ord-149a4824d82046c2a7c8fd528ff214e2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673909B2

Reaction notes

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