Hydrochloric Acid → HCID 178419969, compound

HRID 625632Notes

Reaction equation

HRID 625632 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[C@H:19]([C:20]2[NH:21][CH:22]=[C:23]([C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]=[C:30]([C:35]3[CH:40]=[CH:39][C:38]([C:41]5[N:42]=[C:43]([C@H:46]6[N:50](C(OC(C)(C)C)=O)[C@H:49]7[CH2:58][CH2:59][CH2:60][C@H:48]7[CH2:47]6)[NH:44][CH:45]=5)=[CH:37][CH:36]=3)[CH:29]=[CH:28]4)[N:24]=2)[CH2:18][C@@H:17]2[CH2:61][CH2:62][CH2:63][C@H:16]12)=O)(C)(C)C.C(Cl)Cl>C1(C)C=CC=CC=1>[NH:15]1[C@H:19]([C:20]2[NH:21][CH:22]=[C:23]([C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH:31]=[C:30]([C:35]3[CH:40]=[CH:39][C:38]([C:41]5[N:42]=[C:43]([C@H:46]6[NH:50][C@H:49]7[CH2:58][CH2:59][CH2:60][C@H:48]7[CH2:47]6)[NH:44][CH:45]=5)=[CH:37][CH:36]=3)[CH:29]=[CH:28]4)[N:24]=2)[CH2:18][C@@H:17]2[CH2:61][CH2:62][CH2:63][C@H:16]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 178452533HCID 178452533, compound

Product 1

HCID 178419969HCID 178419969, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4N HCl in dioxane (20 equiv) was added to a solution of (2S,3aS,6aS)-tert-butyl 2-(4-(4-(6-(2-((2S,3aS,6aS)-1-(tert-butoxycarbonyl)-octahydrocyclopenta[b]pyrrol-2-yl)-1H-imidazol-4-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)hexahydrocyclopenta[b]pyrrole-1(2H)-carboxylate in an. DCM and the mixture was stirred at rt for 2-3 h Anhydrous toluene was added to the resultant yellow suspension and then evaporated to dryness to an HCl salt of (2S,3aS,6aS)-2-(4-(4-(6-(2-((2S,3aS,6aS)-octahydrocyclopenta[b]pyrrol-2-yl)-1H-imidazol-4-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)octahydrocyclopenta[b]pyrrole as a beige solid: LC-MS retention time: 2.343 min; m/z 555 (M+H)+.

Workup

  1. additionwas added to the resultant yellow suspension
  2. customevaporated to dryness to an HCl salt of (2S,3aS,6aS)-2-(4-(4-(6-(2-((2S,3aS,6aS)-octahydrocyclopenta[b]pyrrol-2-yl)-1H-imidazol-4-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)octahydrocyclopenta[b]pyrrole as a beige solid

Sources & evidence

ORD record
ord-02d682ef04104991959ee75c3abf53df
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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