(Phenylmethoxy)carbonylamino-3-((1-(3-((1-(triphenylmethyl)imidazol-2-yl)amino)propyl)(1H-indazol-5-yl))carbonylamino)propanoic Acid → HCID 22598956, compound

HRID 2252460Notes

Reaction equation

HRID 2252460 reaction equation
C1(COC([NH:11][CH:12]([CH2:16][NH:17][C:18]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([CH2:29][CH2:30][CH2:31][NH:32][C:33]2[N:34]([C:38]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:35]=[CH:36][N:37]=2)[N:24]=[CH:23]3)=[O:19])[C:13]([OH:15])=[O:14])=O)C=CC=CC=1>C(O)C.[Pd]>[NH2:11][CH:12]([CH2:16][NH:17][C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:29][CH2:30][CH2:31][NH:32][C:33]1[N:34]([C:38]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:35]=[CH:36][N:37]=1)[N:24]=[CH:23]2)=[O:19])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 20707264(Phenylmethoxy)carbonylamino-3-((1-(3-((1-(triphenylmethyl)imidazol-2-yl)amino)propyl)(1H-indazol-5-yl))carbonylamino)propanoic Acid

Product 1

HCID 22598956HCID 22598956, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-((Phenylmethoxy)carbonylamino-3-((1-(3-((1-(triphenylmethyl)imidazol-2-yl)amino)propyl)(1H-indazol-5-yl))carbonylamino)propanoic acid (0.750 g, 1.00 mmol) was added to Pd/C (1.00 g) in ethanol (20 mL). The reaction was evacuated and purged with nitrogen twice. The reaction was then evacuated and purged with hydrogen twice, and then maintained under an atmosphere of hydrogen for 24 h. The reaction was filtered through celite. The filtrate was concentrated to an oil. The oil was recrystallized from hexane:ethyl acetate to give 215.6 mgs (35%) of product. ESMS: Calcd. for C36H35N7O3, 613.28. Found, 614.2 [M+H]+1 Analytical HPLC, Method A, Rt=12.26 min, Purity=90%.

Workup

  1. customThe reaction was evacuated
  2. custompurged with nitrogen twice
  3. customThe reaction was then evacuated
  4. custompurged with hydrogen twice
  5. temperaturemaintained under an atmosphere of hydrogen for 24 h
  6. filtrationThe reaction was filtered through celite
  7. concentrationThe filtrate was concentrated to an oil
  8. customThe oil was recrystallized from hexane

Sources & evidence

ORD record
ord-cf6254cfe8414958a8e4cebe29194b17
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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