Water → HCID 178492391, compound

HRID 343238Notes

Reaction equation

HRID 343238 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][C:18]2([CH3:52])[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:46]=[N:47][CH:48]=[CH:49][CH:50]=3)[C:19]2=[O:51])=[N:9]1)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+].O>CO>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18]2([CH3:52])[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:46]=[N:47][CH:48]=[CH:49][CH:50]=3)[C:19]2=[O:51])=[N:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86753594HCID 86753594, compound

Product 1

HCID 178492391HCID 178492391, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 1.0 g of 2-[3-(1-tert-butoxycarbonyl-1H-Indazol-3-ylmethyl)-3-methyl-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide, prepared as in Intermediate 75, in 10 mL of methanol is added 2.0 g of solid K2CO3. The reaction mixture is stirred 2 h at RT and then 15 mL H2O is added and the reaction mixture stirred 15 min at RT. The resulting white precipitate is filtered, washed with 15 mL of H2O, and dried under vacuum at 90° C. to afford 668 mg of the title compound as a white solid: mp 161°-5° C.; 1H NMR (CDCl3, 400 MHz) δ10.38 (s, br, 1H), 8.55 (s, 1H), 8.48 (m, 1H), 7.74 (d, 1H, J=7.0), 7.42-6.93 (m, 13H), 6.62 (d, 1H, J=8.2), 5.09 (m, 1H), 4.49 (m, 1H), 4.08 (m, 1H), 3.85 (s, 3H), 3.05 (d, 2H, AB quartet, J=15.9), 1.67 (s, 3H), 1.13 (m, 6H); low resolution MS (FAB)m/e 603 (MH+), 424; Anal. (C35H34N6O4) Calcd. C, 69.75; H, 5.69; N, 13.94 Found C, 66.54; H, 5.549; N, 13.19.

Workup

  1. stirringthe reaction mixture stirred 15 min at RT
  2. filtrationThe resulting white precipitate is filtered
  3. washwashed with 15 mL of H2O
  4. customdried under vacuum at 90° C.

Sources & evidence

ORD record
ord-a07cc91f4ce74015837aa4ead55393cf
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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