Hydrochloric Acid → Hydrochloric Acid

HRID 625656Notes

Reaction equation

HRID 625656 reaction equation
[CH3:1][C:2]([CH3:52])([CH3:51])[C@@H:3]([C:12]1[NH:13][C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([C:33]4[NH:37][C:36]([C@@H:38]([NH:43]C(=O)OC(C)(C)C)[C:39]([CH3:42])([CH3:41])[CH3:40])=[N:35][CH:34]=4)=[CH:29][CH:28]=2)[CH:21]=[CH:20]3)=[CH:15][N:16]=1)[NH:4]C(OC(C)(C)C)=O.[ClH:53].O1CCOCC1>C(Cl)Cl>[ClH:53].[NH2:4][C@H:3]([C:12]1[NH:13][C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([C:33]4[NH:37][C:36]([C@@H:38]([NH2:43])[C:39]([CH3:42])([CH3:41])[CH3:40])=[N:35][CH:34]=4)=[CH:29][CH:28]=2)[CH:21]=[CH:20]3)=[CH:15][N:16]=1)[C:2]([CH3:51])([CH3:52])[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58501715HCID 58501715, compound

Product 2

HCID 313Hydrochloric AcidHCID 58501753HCID 58501753, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a reaction mixture of tert-butyl (S)-1-(5-(4-(6-(2-((S)-2,2-dimethyl-1-(tert-butoxycarbonylamino)propyl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-2,2-dimethylpropylcarbamate (0.2 g, 0.283 mmol) in DCM was added 4M hydrogen chloride in dioxane (2 mL, 8 mmol). The reaction mixture was stirred at rt for 4 h and then concentrated to dryness to yield an HCl salt of (S)-1-(5-(4-(6-(2-((S)-1-amino-2,2-dimethylpropyl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-2,2-dimethylpropan-1-amine as a yellow solid. LC-MS (Cond. 1): [M+H]+ 507.43, Rt=3.241 min.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-297429e006444ec888bea8a518be58af
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

Loading…