Trifluoroacetic acid → HCID 68924273, compound

HRID 1186284Notes

Reaction equation

C(N([CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=N)[CH:24]=3)[NH:19][CH:18]=2)[CH2:12]1)C(=O)OC(C)(C)C)C.[C:34](O)([C:36](F)(F)F)=O.[NH4+:41].[OH-:42]>ClCCl>[CH2:34]([NH:41][CH:15]1[CH2:16][CH2:11][CH2:12][CH:13]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=[O:42])[CH:24]=3)[NH:19][CH:18]=2)[CH2:14]1)[CH3:36]

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl ethyl(3-(5-(thiophene-2-carboximidamido)-1H-indol-3-yl)cyclohexyl)carbamate (0.75 g, 1.61 mmol) was treated with 20% 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 solution, 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 (0.50 g, 85%). 1H-NMR (DMSO-d6) δ 1.05 (t, 3H, J=6.9 Hz), 1.44-1.51 (m, 3H), 1.58-1.82 (m, 3H), 1.89-1.97 (m, 2H), 2.58 (q, 2H, J=7.2 Hz), 2.85-2.99 (m, 1H), 3.08-3.23 (m, 1H), 6.19 (s, 2H), 6.62 (d, 1H, J=8.4 Hz), 6.98-7.00 (m, 2H), 7.09 (dd, 1H, J=3.9, 5.1 Hz), 7.26 (d, 1H, J=8.4 Hz), 7.58 (d, 1H, J=5.1 Hz), 7.70 (d, 1H, J=3.0 Hz), 10.54 (s, 1H); ESI-MS (m/z, %) 367 (MH+, 50%), 322 (100), ESI-HRMS (MH+) calc. for C21H27N4S, calculated: 367.1950. found: 367.1956.

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-ef0c491689df44a68f0d3a32327b8f75
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673909B2

Reaction notes

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