Hydrochloric Acid → HCID 178492386, compound

HRID 343242Notes

Reaction equation

HRID 343242 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:38]([CH3:40])[CH3:39])[C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[O:28])[C:22]3[CH:41]=[CH:42][CH:43]=[CH:44][C:21]=3[N:20]([C:45]3[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=3)[C:19]2=[O:51])=[N:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[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:38]([CH3:40])[CH3:39])[C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[O:28])[C:22]3[CH:41]=[CH:42][CH:43]=[CH:44][C:21]=3[N:20]([C:45]3[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=3)[C:19]2=[O:51])=[N:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67696995HCID 67696995, compound

Product 1

HCID 178492386HCID 178492386, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 487 mg (0.83 mmol) of 2-[3-(1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-pyridin-4-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl) acetamide, prepared as in Intermediate 76, is added 8 mL of a 4N solution of HCl in dioxane. The reaction is stirred overnight at RT. The reaction is concentrated, then purified by silica gel flash column chromatography (gradient 3:1-4:1 ethyl acetate:hexanes) to afford 245 mg of the title compound as an oil. This oil is triturated with hexane/ethyl acetate to afford a white powder: 1H NMR (CDCl3, 400 MHz) δ8.56 (s, br, 2H), 7.82 (d, 1H, J=8.0), 7.39-7.29 (m, 6H) 7.17-7.10 (m, 3H) 6.93 (dd, 2H, J=2.1,8.5) 4.93 (m, 1H), 4.39 (d, br, 1H, J=16.1) 4.25-4.19 (m, 2H) 3.82 (s, 3H) 3.77 (m, 1H) 3.58 (dd, 1H, J=5.8, 16.2) 1.02 (dd, 6H, J=3.9, 6.6); low resolution MS (FAB)m/e 589 (MH+).

Workup

  1. concentrationThe reaction is concentrated
  2. custompurified by silica gel flash column chromatography (gradient 3:1-4:1 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-4576415375fe4a5e8bb75b954a4976b8
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

Loading…