Triphenylphosphine → HCID 178428088, compound

HRID 2280420Notes

Reaction equation

HRID 2280420 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([C:6](/[N:8]=[C:9](\[NH:16][C:17]2[NH:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH:18]=2)/[NH:10][C:11]([CH3:15])([CH3:14])[CH2:12]O)=[O:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:1][C:2]1[CH:30]=[CH:29][C:5]([C:6](/[N:8]=[C:9]2\[NH:16][C:17]3[N:21]([N:20]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH:18]=3)[CH2:12][C:11]([CH3:15])([CH3:14])[NH:10]\2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178454582HCID 178454582, compound

Product 1

HCID 178428088HCID 178428088, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-4-fluoro-N-(((3-(4-fluorophenyl)-1H-pyrazol-5-yl)amino)((1-hydroxy-2-methylpropan-2-yl)amino)methylene)benzamide (25 mg, 0.06 mmol) in anhydrous THF (0.5 mL) under a nitrogen atmosphere was added triphenylphosphine (19 mg, 0.07 mmol) followed by diisopropyl azodicarboxylate (DIAD) (14 μL, 0.07 mmol). The reaction mixture was stirred at room temperature for 30 minutes and purification by silica chromatography (EtOAc:hexanes) afforded the title compound (21 mg, 88% yield). LCMS (ESI). found (M-H)−, 394.15; 1H NMR (400 MHz, DMSO-d6) δ 12.91 (s, 1H), 9.35 (s, 1H), 8.18 (m, 2H), 7.75 (m, 2H), 7.31 (m, 4H), 7.17 (s, 1H), 3.75 (s, 2H), 1.39 (s, 6H).

Workup

  1. custompurification by silica chromatography (EtOAc:hexanes)

Sources & evidence

ORD record
ord-21ba86f51fce4239a8ecd4be21123533
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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