Hydrochloric Acid → HCID 67387160, compound

HRID 1027142Notes

Reaction equation

HRID 1027142 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[NH:34][C:33]([C@@H:35]5[CH:39]=[C:38]([CH2:40]C)[CH2:37][N:36]5C(OC(C)(C)C)=O)=[N:32][CH:31]=4)=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C.Cl.C(C1CN[C@H](C2NC(C3C=CC(C4C=CC(C5NC([C@@H]6CCCN6)=NC=5)=CC=4)=CC=3)=CN=2)C=1)C>O1CCOCC1>[CH3:40][C:38]1[CH2:37][NH:36][C@H:35]([C:33]2[NH:34][C:30]([C:27]3[CH:28]=[CH:29][C:24]([C:21]4[CH:20]=[CH:19][C:18]([C:15]5[NH:14][C:13]([C@@H:9]6[CH2:10][CH2:11][CH2:12][NH:8]6)=[N:17][CH:16]=5)=[CH:23][CH:22]=4)=[CH:25][CH:26]=3)=[CH:31][N:32]=2)[CH:39]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67386639HCID 67386639, compoundHCID 67387191HCID 67387191, compound2×

Product 1

HCID 67387160HCID 67387160, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (S)-tert-butyl 2-(5-(4′-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)-4-ethyl-2H-pyrrole-1(5H)-carboxylate (intermediate 26) (0.171 g, 0.248 mmol) in dioxane (4 mL) was added a solution of 5.5N HCl in dioxane (2.5 mL) at 0° C. The mixture was stirred at room temperature for 20 hours. The resulting mixture was concentrated to give 2-((S)-4-methyl-2,5-dihydro-1H-pyrrol-2-yl)-5-(4′-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazole (Intermediate 29) (0.121 g, yield: 83%) as a brown solid. ES LC-MS m/z=451 (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated

Sources & evidence

ORD record
ord-95c1fe3a1144432985670282de9a50bb
Source dataset
uspto-grants-2014_05
Patent number
US08729077B2

Reaction notes

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