Trifluoroacetic acid → HCID 178457885, compound

HRID 343233Notes

Reaction equation

HRID 343233 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]2[C:24](=[O:25])[N:23]([CH2:26][C:27]([N:29]([CH:36]([CH3:38])[CH3:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:28])[C:22]3[CH:39]=[CH:40][CH:41]=[CH:42][C:21]=3[N:20]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:19]2=[O:49])=[N:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]2[C:24](=[O:25])[N:23]([CH2:26][C:27]([N:29]([CH:36]([CH3:38])[CH3:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:28])[C:22]3[CH:39]=[CH:40][CH:41]=[CH:42][C:21]=3[N:20]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:19]2=[O:49])=[N:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 107705992-[3-(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-phenyl-acetamide

Product 1

HCID 178457885HCID 178457885, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

400 mg of 2-[3-(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-phenyl-acetamide, prepared as in Intermediate 68, is dissolved in 10 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 and the residue is purified by flash column chromatography on silica gel (MeOH 1%:CHCl3 99%) to afford 240 mg of the title compound: 1H NMR (400 MHz, CDCl3) δ7.93 (d, 1H, J=8.4), 7.51-7.19 (m, 16H), 6.99 (m, 1H), 5.03 (m,1H, J=6.8), 4.29 (d, 1, J=16.4), 4.26 (d, 1H, J=16.4), 4.14 (m, 1H), 3.89 (dd, 1H, J=16.5, 6.4), 3.82 (dd 1H,J=16.5, 6.4,), 1.08 (t, 6H, J=6.8); LOW RESOLUTION MS (FAB) m/e 558 (MH+); Tr =9.90 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 flash column chromatography on silica gel (MeOH 1%:CHCl3 99%)

Sources & evidence

ORD record
ord-91125ba28ee04520995f778dc394261b
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

Loading…