Hydrochloric Acid → HCID 86657594, compound

HRID 1040569Notes

Reaction equation

HRID 1040569 reaction equation
C([O:5][C:6](=[O:57])[CH2:7][CH2:8][C@H:9]([NH:23][C:24]([C:26]1[N:30]2[C@:31]([CH3:56])([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([O:51][C:52]([F:55])([F:54])[F:53])=[CH:47][CH:46]=3)[C:32](=[O:43])[N:33]([C:34]3[CH:39]=[C:38]([Cl:40])[C:37]([F:41])=[C:36]([Cl:42])[CH:35]=3)[C:29]2=[N:28][CH:27]=1)=[O:25])[C:10](=[O:22])[NH:11][C:12]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH2:13][CH3:14])(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[Cl:40][C:38]1[CH:39]=[C:34]([N:33]2[C:29]3=[N:28][CH:27]=[C:26]([C:24]([NH:23][C@H:9]([C:10](=[O:22])[NH:11][C:12]([CH3:21])([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[CH2:13][CH3:14])[CH2:8][CH2:7][C:6]([OH:57])=[O:5])=[O:25])[N:30]3[C@:31]([CH3:56])([CH2:44][C:45]3[CH:46]=[CH:47][C:48]([O:51][C:52]([F:54])([F:53])[F:55])=[CH:49][CH:50]=3)[C:32]2=[O:43])[CH:35]=[C:36]([Cl:42])[C:37]=1[F:41]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 86657595HCID 86657595, compound

Product 1

HCID 86657594HCID 86657594, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-{[(R)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxy-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-4-(1-methyl-1-pyridin-2-yl-propylcarbamoyl)-butyric acid tert-butyl ester (116 mg, 0.142 mmol) in 2 mL of CH2Cl2 was added HCl in dioxane (0.177 mL, 0.708 mmol). The reaction mixture was stirred at room temperature for 6 h. An additional portion of HCl in dioxane (0.177 mL, 0.708 mmol) was added, and the reaction mixture was stirred for 4 h and then concentrated to a colorless oil. The residue was purified by reverse-phase HPLC (20-90% CH3CN/H2O, 0.1% TFA) to give 45 mg (42%) of the title compound, isolated as the TFA salt, m/z 763.8 [M+1]+.

Workup

  1. stirringthe reaction mixture was stirred for 4 h
  2. concentrationconcentrated to a colorless oil
  3. customThe residue was purified by reverse-phase HPLC (20-90% CH3CN/H2O, 0.1% TFA)

Sources & evidence

ORD record
ord-8dd783f746bd477cb764f60691e18fae
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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