HCID 178461192, compound → HCID 178461193, compound

HRID 1509685Notes

Reaction equation

HRID 1509685 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH3:13])[CH2:11][CH2:10][C@H:9]1[C:14]1[NH:18][C:17]2[C:19]3[C:24]([CH2:25][CH2:26][C:16]=2[N:15]=1)=[CH:23][C:22]1[C:27]2[C:32]([CH2:33][O:34][C:21]=1[CH:20]=3)=[CH:31][C:30]([C:35]1[NH:39][C:38]([C@@H:40]3[CH2:44][CH2:43][C@H:42]([CH3:45])[N:41]3[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[N:37][CH:36]=1)=[CH:29][CH:28]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1[C@@H](C)CC[C@H]1C1NC2C3C(C=CC=2N=1)=CC1C2C(COC=1C=3)=CC(C1NC([C@@H]3CC[C@H](C)N3C(OC(C)(C)C)=O)=NC=1)=CC=2)=O)(C)(C)C>C(Cl)Cl.O=[Mn]=O>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH3:13])[CH2:11][CH2:10][C@H:9]1[C:14]1[NH:18][C:17]2[C:19]3[C:24]([CH:25]=[CH:26][C:16]=2[N:15]=1)=[CH:23][C:22]1[C:27]2[C:32]([CH2:33][O:34][C:21]=1[CH:20]=3)=[CH:31][C:30]([C:35]1[NH:39][C:38]([C@@H:40]3[CH2:44][CH2:43][C@H:42]([CH3:45])[N:41]3[C:46]([O:48][C:49]([CH3:51])([CH3:50])[CH3:52])=[O:47])=[N:37][CH:36]=1)=[CH:29][CH:28]=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178461192HCID 178461192, compound

Product 1

HCID 178461193HCID 178461193, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Tert-butyl (2S,5S)-2-(5-{2-[(2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidin-2-yl]-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate Tert-butyl (2S,5S)-2-(9-{2-[(2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidin-2-yl]-1H-imidazol-5-yl}-1,4,5,11-tetrahydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate (393 mg, 0.55 mmol) was suspended in DCM (7 mL) and activated MnO2 (1.45 g, 16.7 mmol) was added in a single portion. The reaction mixture was heated to 40° C. After stirring for 2.5 h, the mixture was cooled to rt and the slurry was filtered over celite. The filter cake was washed with copious CH2Cl2 and MeOH and the filtrate was concentrated under reduced pressure. The crude material was taken on to the next step without further purification to afford tert-butyl (2S,5S)-2-(5-{2-[(2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidin-2-yl]-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate (328 mg, 85%).

Workup

  1. temperaturethe mixture was cooled to rt
  2. filtrationthe slurry was filtered over celite
  3. washThe filter cake was washed with copious CH2Cl2 and MeOH
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude material was taken on to the next step without further purification

Sources & evidence

ORD record
ord-2cb56dc8067e4c6d970bdc30b51e2adf
Source dataset
uspto-grants-2015_12
Patent number
US09221833B2

Reaction notes

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