Trifluoroacetic acid → HCID 66604444, compound

HRID 2410858Notes

Reaction equation

HRID 2410858 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:11]1[CH:12]=[C:13]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH3:47])[CH:41]=2)[CH:14]=[C:15]2[C:23]=1[NH:22][C:21]1[CH:20]=[C:19]([C:24]([N:26]3[CH2:32][CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[O:25])[CH:18]=[CH:17][C:16]2=1)(=[O:10])[NH2:9]>C(Cl)Cl>[N:26]1([C:24]([C:19]2[CH:20]=[C:21]3[C:16]([C:15]4[CH:14]=[C:13]([C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH3:47])[CH:41]=5)[CH:12]=[C:11]([C:8]([NH2:9])=[O:10])[C:23]=4[NH:22]3)=[CH:17][CH:18]=2)=[O:25])[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46832735HCID 46832735, compound

Product 1

HCID 66604444HCID 66604444, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of tert-butyl 4-(8-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carbonyl)-1,4-diazepane-1-carboxylate (11 mg, 0.020 mmol) in DCM (5 mL). After 4 hr at RT, the solvents were removed and the residue was taken up in MeOH and applied onto a SCX cartridge. This was washed with MeOH and released 2 N NH3 in MeOH to leave 7-(1,4-diazepane-1-carbonyl)-3-(3-methoxyphenyl)-9H-carbazole-1-carboxamide (8.5 mg, 0.019 mmol, 92% yield) as a solid. MS (ESI) m/z 443.23 (M+H). 1H NMR (500 MHz, MeOD) δ ppm 8.57 (1H, s), 8.28 (1H, d, J=8.24 Hz), 8.24 (1H, s), 7.71 (1H, s), 7.34-7.44 (3H, m), 7.29 (1H, d, J=7.93 Hz), 6.94 (1H, dt, J=7.55, 2.02 Hz), 3.92 (3H, s), 3.81-3.89 (2H, m), 3.55-3.65 (2H, m), 3.10-3.18 (1H, m), 2.94-3.04 (2H, m), 2.87-2.95 (1H, m), 1.96-2.08 (1H, m), 1.77-1.89(1H, m).

Workup

  1. customthe solvents were removed
  2. washThis was washed with MeOH

Sources & evidence

ORD record
ord-e2532a81b7e6458facad7893a4a098da
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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