1,4-Dioxane hydrochloride → HCID 178461571, compound

HRID 1625512Notes

Reaction equation

HRID 1625512 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH3:13])[CH2:10][C@H:9]1[C:14]1[NH:18][C:17]2[CH:19]=[CH:20][C:21]([C:23]#[C:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[N:32]=[C:33]([C@@H:36]5[CH2:40][C@H:39]([CH3:41])[CH2:38][N:37]5C(OC(C)(C)C)=O)[NH:34][CH:35]=4)=[CH:27][CH:26]=3)=[CH:22][C:16]=2[N:15]=1)=O)(C)(C)C.[ClH:49].O1CCOCC1>CO>[ClH:49].[CH3:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([C:23]#[C:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]5[N:32]=[C:33]([C@@H:36]6[CH2:40][C@H:39]([CH3:41])[CH2:38][NH:37]6)[NH:34][CH:35]=5)=[CH:29][CH:30]=4)=[CH:22][C:16]=3[N:15]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178461451HCID 178461451, compound

Product 1

HCID 178461571HCID 178461571, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (2S,4S)-2-[4-[4-[2-[2-[(2S,4S)-1-tert-butoxycarbonyl-4-methyl-pyrrolidin-2-yl]-1H-benzimidazol-5-yl]ethynyl]phenyl]-1H-imidazol-2-yl]-4-methyl-pyrrolidine-1-carboxylate (56 mg, 0.086 mmol) in methanol (2 mL) is added 4M HCl/dioxane (430 uL, 1.72 mmol). The mixture is stirred at rt for 3 hours. Removal of the solvent under vacuum gives 2-[(2S,4S)-4-methylpyrrolidin-2-yl]-5-[2-[4-[2-[(2S,4S)-4-methylpyrrolidin-2-yl]-1H-imidazol-4-yl]phenyl]ethynyl]-1H-benzimidazole HCl salt. The crude is used directly in the next step.

Workup

  1. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-c826021ad00041e5bdf0fc09dc3eb13c
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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