1,2-Diaminocyclohexane, trans- → HCID 66576896, compound

HRID 572454Notes

Reaction equation

HRID 572454 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.Cl[C:17]1[CH:22]=[C:21](I)[CH:20]=[C:19]([C:24]([F:27])([F:26])[F:25])[N:18]=1.[C@@H:28]1(N)[CH2:33][CH2:32]CC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:32]1([C:17]2[CH:22]=[C:21]([N:12]3[CH2:13][CH2:14][N:10]([C:5]4[CH:6]=[N:7][CH:8]=[CH:9][C:4]=4[CH:1]4[CH2:3][CH2:2]4)[C:11]3=[O:15])[CH:20]=[C:19]([C:24]([F:27])([F:26])[F:25])[N:18]=2)[CH2:33][CH2:28]1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 108597852-Chloro-4-iodo-6-(trifluoromethyl)pyridineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 66576896HCID 66576896, compoundYield 502.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 260 mg, 1.2807 mmol) was reacted with 2-chloro-4-iodo-6-(trifluoromethyl)pyridine (471 mg, 1.5369 mmol), copper iodide (24 mg, 0.1280 mmol), trans-cyclohexane-1,2-diamine (15 mg, 0.1280 mmol), potassium phosphate (816 mg, 3.8421 mmol) and 1,4-dioxane (5 mL) to afford crude product. Purification by column chromatography on silica gel (1% methanol in chloroform) afforded 250 mg of pure product (51.1% yield). 1HNMR (CDCl3, 400 MHz): δ 8.55-8.42 (bs, 2H), 7.64-7.62 (d, 2H), 6.85 (s, 1H), 4.13-4.02 (m, 4H), 2.10-1.98 (m, 2H), 1.18-0.99 (m, 6H), 0.87-0.83 (m, 2H). LCMS: 98.89%, m/z=388.9 (M+1). HPLC: 99.67%.

Workup

  1. customreagents and reaction conditions
  2. customto afford crude product
  3. customPurification by column chromatography on silica gel (1% methanol in chloroform)

Sources & evidence

ORD record
ord-171c6c283adf43fa937f8152a7c4036b
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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