Triethylamine → HCID 178481728, compound

HRID 1465704Notes

Reaction equation

HRID 1465704 reaction equation
[CH2:1](N(CC)CC)C.Cl.[Br:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19](=[NH:23])OCC)[CH:17]=2)[NH:12][N:11]=1.C[NH:25][NH:26][C:27]([C@@H:29]1[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]1)=O>CCO>[Br:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[N:23]=[C:27]([C@@H:29]4[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]4)[N:26]([CH3:1])[N:25]=3)[CH:17]=2)[NH:12][N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86695581(R)-tert-butyl 3-(2-methylhydrazinecarbonyl)piperidine-1-carboxylateHCID 178468222HCID 178468222, compound

Product 1

HCID 178481728HCID 178481728, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Added triethylamine (0.5 ml, 3.59 mmol) to a solution of ethyl 3-bromo-1H-indazole-5-carbimidate hydrochloride (200 mg, 0.658 mmol) and (R)-tert-butyl 3-(2-methylhydrazine-carbonyl)piperidine-1-carboxylate (200 mg, 0.78 mmol) in EtOH (USP, 5 ml) and heated in a microwave oven at 100° C. for 12 hours. Evaporated solvent then chromatographed residue on silica gel eluting with 1/1 v/v EtOAc/Hexanes to yield (R)-tert-butyl 3-(3-(3-bromo-1H-indazol-5-yl)-1-methyl-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate as a white solid (100 mg).

Sources & evidence

ORD record
ord-feb8759b7bef45bdbe2d0c79b26aae80
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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