Hydrochloric Acid → HCID 178492385, compound

HRID 343228Notes

Reaction equation

HRID 343228 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[S:46][CH:47]=[CH:48][CH:49]=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[S:46][CH:47]=[CH:48][CH:49]=3)[C:19]2=[O:50])=[N:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 867535902-[3-(1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-thiophen-2-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

Product 1

HCID 178492385HCID 178492385, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 280 mg (0.40 mmol) of crude 2-[3-(1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-thiophen-2-yl-2,3,4,5-tetrahydro-benzo [b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide, prepared as in Intermediate 60, is added 10 mL of 4N HCl in dioxane at RT. The resulting solution is stirred 3 h and 100 mL of Et2O is added. The Et2O is decanted away from the gum. The gum is washed with Et2O and purified by RP-HPLC (30-60% acetonitrile/H2O over 30 min) to afford 23.7 mg of the title compound: 1H NMR (CDCl3, 300 MHz) δ7.83 (d, 1H, J=8.0), 7.45-7.06 (m, 11H), 6.96-6.79 (m, 4H), 4.97 (m, 1H), 4.31 (d, 1H, J=16.6), 4.20 (m, 1H), 4.08 (d, 1H, J=16.6), 3.81 (s, 3H), 3.73 (m, 2H), 1.05 (d, 3H, J=6.8), 1.02 (d, 3H, J=6.8); low resolution MS (FAB) m/e 594 (MH+); RP-HPLC Tr =22.0 min (30-60% acetonitrile/ H2O).

Workup

  1. customThe Et2O is decanted away from the gum
  2. washThe gum is washed with Et2O
  3. custompurified by RP-HPLC (30-60% acetonitrile/H2O over 30 min)

Sources & evidence

ORD record
ord-8e03234d1e25459d8de423d7ca831281
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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