Trifluoroacetic acid → HCID 178457889, compound

HRID 343235Notes

Reaction equation

HRID 343235 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][CH:19]3[C:25](=[O:26])[N:24]([CH2:27][C:28]([N:30]([CH:42]([CH3:44])[CH3:43])[C:31]4[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=4)=[O:29])[C:23]4[CH:45]=[CH:46][CH:47]=[CH:48][C:22]=4[N:21]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:20]3=[O:55])=[N:7][N:8]2C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][CH:19]3[C:25](=[O:26])[N:24]([CH2:27][C:28]([N:30]([CH:42]([CH3:44])[CH3:43])[C:31]4[CH:32]=[CH:33][C:34]([O:37][C:38]([F:39])([F:40])[F:41])=[CH:35][CH:36]=4)=[O:29])[C:23]4[CH:45]=[CH:46][CH:47]=[CH:48][C:22]=4[N:21]([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)[C:20]3=[O:55])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867535932-[3-(6-Fluoro-1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-trifluoromethoxy-phenyl)-acetamide

Product 1

HCID 178457889HCID 178457889, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

70 mg of 2-[3-(6-Fluoro-1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-trifluoromethoxy-phenyl)-acetamide, prepared as in Intermediate 70, is dissolved in 2 mL of CHCl3 and 5 mL of TFA is added. The reaction mixture is stirred for 6 h and the solvents were removed in vacuo. The residue is purified by silica gel flash column chromatography using hexane/EtOAc 40:60 as eluent to afford the 40 mg of the title compound: 1H NMR (400 MHz, DMSO-d6) δ7.73 (dd, 1H, J=8.9, 5.1), 7.41-7.18 (m, 12H), 7.08 (dd, 1H, J=7.3, 2.0), 6.97 (dd, 1H, J=8.9, 1.7), 6.92 (dd, 1H, J=7.2, 2.0), 6.84 (dd, 1H,J=9.1, 2.0), 5.01 (m, 1H), 4.22 (m, 3H), 3.75 (dd, 1H, J=16.5, 6.4), 3.56 (dd, 1H, J=16.5, 6.4), 1.06 (t, 6H, J=6.8); low resolution MS (FAB) m/e 660 (MH+); Tr =12.32 min. (HPLC Column: Dynamax C-8 2 mL/min., 50-90% Acetonitrile in aqueous TFA (0.1% v/v) over 15 min.).

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue is purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-b8c7ebc42a664f46a4d7e77d3249dcac
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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