Hydrochloric Acid → (R)-5-(1-methyl-5-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole

HRID 1465706Notes

Reaction equation

HRID 1465706 reaction equation
Cl.[CH3:2][N:3]1[C:7]([C@@H:8]2[CH2:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[N:6][C:5]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[C:24]3[C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[N:4]1>O1CCOCC1.C(Cl)Cl>[CH3:2][N:3]1[C:7]([C@@H:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[N:6][C:5]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[C:24]3[C:30]2[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=2)=[N:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67517332(R)-tert-butyl 3-(1-methyl-3-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 86695582(R)-5-(1-methyl-5-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazoleYield 77.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Added 4M HCl in dioxane (2 ml) to a solution of (R)-tert-butyl 3-(1-methyl-3-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate (25 mg, 0.054 mmol) in DCM (5 ml), then stirred 4 hours at room temperature. The solvent was evaporated to yield (R)-5-(1-methyl-5-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole as a white solid (15 mg).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-dddf7761a0fd432ab8530ede7e6717f5
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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