Trimethylsilyl iodide → HCID 67451810, compound

HRID 869157Notes

Reaction equation

HRID 869157 reaction equation
[F:1][C:2]1[C:3]([C:8]2([CH2:12][NH:13][C:14]3[N:19]=[N:18][C:17]([C:20]4[CH:21]=[C:22]5[C:26](=[CH:27][CH:28]=4)[NH:25][N:24]=[C:23]5[NH:29][CH2:30][CH2:31][NH:32]C(=O)OCC4C=CC=CC=4)=[CH:16][CH:15]=3)[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Si](I)(C)(C)C>C(#N)C.CO>[F:1][C:2]1[C:3]([C:8]2([CH2:12][NH:13][C:14]3[N:19]=[N:18][C:17]([C:20]4[CH:21]=[C:22]5[C:26](=[CH:27][CH:28]=4)[NH:25][N:24]=[C:23]5[NH:29][CH2:30][CH2:31][NH2:32])=[CH:16][CH:15]=3)[CH2:9][CH2:10][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67454077HCID 67454077, compound

Product 1

HCID 67451810HCID 67451810, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Benzyl 2-(5-(6-((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)-1H-indazol-3-ylamino)ethylcarbamate (48 mg, 84 μmol) was dissolved in acetonitrile (5 mL), and TMSI (0.5 mL) was added. The reaction was stirred for 15 min, diluted with methanol (15 mL), concentrated, and was directly purified by reverse phase column chromatography to yield 20 mg (88%) of N1-(5-(6-((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)-1H-indazol-3-yl)ethane-1,2-diamine as a yellow solid, m/z=433 [M+H].

Workup

  1. concentrationconcentrated
  2. customwas directly purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-68db51973d244a919404f57efbe15a91
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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