Hydrochloric Acid → HCID 178457886, compound

HRID 343226Notes

Reaction equation

HRID 343226 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]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH:30]([CH3:32])[CH3:31])=[O:28])[C:22]3[CH:40]=[CH:41][CH:42]=[CH:43][C:21]=3[N:20]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:19]2=[O:50])=[N:9]1)=O)(C)(C)C.Cl.CCOCC>O1CCOCC1>[F:39][C:36]1[CH:37]=[CH:38][C:33]([N:29]([CH:30]([CH3:32])[CH3:31])[C:27](=[O:28])[CH2:26][N:23]2[C:24](=[O:25])[CH:18]([CH2:17][C:10]3[C:11]4[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][N:9]=3)[C:19](=[O:50])[N:20]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:21]3[CH:43]=[CH:42][CH:41]=[CH:40][C:22]2=3)=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 105803742-[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-(4-fluoro-phenyl)-N-isopropyl-acetamide

Product 1

HCID 178457886HCID 178457886, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 890 mg (1.3 mmol) of crude 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-(4-fluoro-phenyl)-N-isopropyl-acetamide, prepared as in Intermediate 58, 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 (50-60% acetonitrile/ H2O over 30 min) to afford 86.7 mg of the title compound: 1H NMR (CDCl3, 300 MHz) δ7.85 (d, 1H, J=8.2), 7.43-7.09 (m, 15H), 6.96 (d, 1H, J=8.3), 5.01 (m, 1H), 4.98 (m, 2H), 3.82 (m, 2H), 1.05 (m, 6H); low resolution MS (FAB) m/e 576 (MH+); RP-HPLC Tr =5.5 min (40-60% acetonitrile/ H2O).

Workup

  1. filtrationThe precipitate is filtered
  2. custompurified by RP-HPLC (50-60% acetonitrile/ H2O over 30 min)

Sources & evidence

ORD record
ord-a76a4a50572446ff87ca3725b68dafe3
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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