Hydrochloric Acid → HCID 178492387, compound

HRID 343227Notes

Reaction equation

HRID 343227 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:49]=[CH:48][S:47][CH:46]=3)[C:19]2=[O:50])=[N:9]1)=O)(C)(C)C.Cl.CCOCC>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:49]=[CH:48][S:47][CH:46]=3)[C:19]2=[O:50])=[N:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 676963882-[3-(1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-thiophen-3-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

Product 1

HCID 178492387HCID 178492387, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 590 mg (0.80 mmol) of crude 2-[3-(1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-thiophen-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 59, is added 10 mL of 4N HCl in dioxane at RT. The resulting solution is stirred 4 h and 100 mL of Et2O is added. The precipitate is filtered and purified by RP-HPLC (30-60% acetonitrile/ H2O over 30 min) to afford 71 mg of the title compound: 1H NMR (DMSO-d6, 300 MHz) δ7.78 (d, 1H, J=8.1), 7.59-7.24 (m, 9H), 7.06 (m, 9H), 4.75 (m, 1H), 4.47 (d, 1H, J=17.1), 4.15 (m, 3H), 3.82 (s, 3H), 3.44 (m, 2H), 0.98 (d, 3H, J=6.9), 0.94 (d, 3H, J=6.9); low resolution MS (FAB) m/e 594 (MH+); RP-HPLC Tr =16.2 min (30-60% acetonitrile/ H2O).

Workup

  1. filtrationThe precipitate is filtered
  2. custompurified by RP-HPLC (30-60% acetonitrile/ H2O over 30 min)

Sources & evidence

ORD record
ord-9c71e13867094cc4a06adc817a58243b
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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