Hydrochloric Acid → methyl [4-(2-{(2S,4R)-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinyl}-1H-imidazol-5-yl)phenyl]carbamate hydrochloride

HRID 1053835Notes

Reaction equation

HRID 1053835 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15]([C@@H:17]3[CH2:21][C@H:20]([CH:22]4[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]4)[CH2:19][N:18]3C(OC(C)(C)C)=O)=[N:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:4].[ClH:39]>O1CCOCC1>[ClH:39].[CH3:31][S:28]([N:25]1[CH2:24][CH2:23][CH:22]([C@@H:20]2[CH2:19][NH:18][C@H:17]([C:15]3[NH:16][C:12]([C:9]4[CH:8]=[CH:7][C:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])=[CH:11][CH:10]=4)=[CH:13][N:14]=3)[CH2:21]2)[CH2:27][CH2:26]1)(=[O:29])=[O:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317363052-methyl-2-propanyl (2S,4R)-2-(5-{4-[(methoxycarbonyl)amino]phenyl}-1H-imidazol-2-yl)-4-[1-(methylsulfonyl)-4-piperidinyl]-1-pyrrolidinecarboxylate

Product 1

HCID 131736307methyl [4-(2-{(2S,4R)-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinyl}-1H-imidazol-5-yl)phenyl]carbamate hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of the compound prepared in Example 64 (0.447 g, 0.811 mmol) in 1,4-dioxane was added 4 M HCl in 1,4-dioxane (5.0 mL) and the reaction mixture stirred at room temperature for 1 h. The mixture was concentrated and the residue was purified by trituration with 1:1 dichloromethane/hexanes to afford the title compound (0.46 g, 99%) as a light brown solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by trituration with 1:1 dichloromethane/hexanes

Sources & evidence

ORD record
ord-e6372521717b4c99b53138070f129a58
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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