2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57666167, compound

HRID 602963Notes

Reaction equation

HRID 602963 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[N:4]=[CH:5][C:6]2[CH2:11][N:10]([C@@H:12]3[CH2:17][C@H:16]([NH:18]C(=O)OCC4C=CC=CC=4)[C@@H:15]([C:29]4[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:30]=4[F:37])[CH2:14][CH2:13]3)[CH2:9][C:7]=2[N:8]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[F:39][C:2]([F:1])([F:38])[C:3]1[N:4]=[CH:5][C:6]2[C:7](=[CH:9][N:10]([C@@H:12]3[CH2:17][C@H:16]([NH2:18])[C@@H:15]([C:29]4[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:30]=4[F:37])[CH2:14][CH2:13]3)[CH:11]=2)[N:8]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86629789HCID 86629789, compound

Product 1

HCID 57666167HCID 57666167, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of benzyl [(1S,2R,5S)-5-[2-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidin-6-yl]-2-(2,4,5-trifluorophenyl)cyclohexyl]carbamate (265 mg) and DDQ (111 mg) in 4 nm of dioxane was stirred for 4 h and the resulting product purified by chromatography on a Biotage Horizon® system (silica, gradient 10-35% ethyl acetate/dichloromethane) to give the title compound. LC-MS 549.3 (M+1). A portion of this product (20 mg) was dissolved in acetonitrile (2 mL), treated with trimethylsilyl iodide (0.2 mL), stirred for 30 min, and quenched with methanol (2 mL). The desired product was purified by preparative TLC (silica, 1:9:90 ammonium hydroxide:methanol:dichloromethane). LC-MS 415.3.

Workup

  1. customthe resulting product purified by chromatography on a Biotage Horizon® system (silica, gradient 10-35% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-0218362e3d784848a1cfeef802328b38
Source dataset
uspto-grants-2011_03
Patent number
US07906649B2

Reaction notes

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