Benzyl Bromide → HCID 86718554, compound

HRID 1485031Notes

Reaction equation

HRID 1485031 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:16]3[N:17]([C:30]([CH3:33])=[N:31][N:32]=3)[N:18]=[C:19]([C:21]3[NH:22][C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:16]3[N:17]([C:30]([CH3:33])=[N:31][N:32]=3)[N:18]=[C:19]([C:21]3[N:22]([CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 136408088HCID 136408088, compound

Product 1

HCID 86718554HCID 86718554, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[6-(1H-Indol-2-yl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (71.00 mg; 0.16 mmol) was suspended in 300 μl THF and treated with NaH (10.19 mg; 0.26 mmol; 60% in mineral oil). After 10 minutes of stilling, Benzyl bromide (19.17 μl; 0.16 mmol) was added and stirred for 16 hours. The crude material was purified via flash chromatography and afterwards with reversed phase chromatography under basic conditions.

Workup

  1. customThe crude material was purified via flash chromatography and afterwards with reversed phase chromatography under basic conditions

Sources & evidence

ORD record
ord-3a87ca1aa38149a597a4259389b11462
Source dataset
uspto-grants-2016_08
Patent number
US09422290B2

Reaction notes

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