1,2-Diaminocyclohexane, trans- → HCID 44183500, compound

HRID 1966398Notes

Reaction equation

HRID 1966398 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH:20]=[CH:19][NH:18][C:16]=3[N:17]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].BrC1C=CC([CH2:28][S:29](CC2C=CC(Br)=CC=2)(=[O:31])=[O:30])=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N[C@@H:49]1[CH2:54][CH2:53][CH2:52][CH2:51][C@H:50]1N>O1CCOCC1.[Cu]I>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH:20]=[CH:19][N:18]([C:53]4[CH:52]=[CH:51][C:50]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:49][CH:54]=4)[C:16]=3[N:17]=2)=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 2674191,1'-[Sulfonylbis(methylene)]bis(4-bromobenzene)HCID 68639256(4-Isopropoxy-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-2-yl)-amine

Product 1

HCID 44183500HCID 44183500, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

In a sealed tube, (4-Isopropoxy-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-2-yl)-amine (350 mg, 1.17 mmol), 4-bromophenylmethylsulfone (552 mg, 2.35 mmol), CuI (68.4 mg, 0.352 mmol), and K3PO4 (763 mg, 3.52 mmol) are suspended in 1,4-dioxane (10 mL). Then, trans-1,2-diaminocyclohexane (42.7 μL, 0.352 mmol) is added at rt. The reaction vial is flushed with Ar and the mixture is heated to 110° C. for 6 h. After cooling to rt, the reaction mixture is diluted with EtOAc and the organic layer is washed with saturated aqueous NaCl solution (3×). The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by reverse phase prep-HPLC (Waters) to afford the title compound (3) as an off-white solid. HPLC: tR=1.67 min (Method A); MS-ES: (M+H)+=423.

Workup

  1. customThe reaction
  2. customvial is flushed with Ar
  3. temperatureAfter cooling to rt
  4. additionthe reaction mixture is diluted with EtOAc
  5. washthe organic layer is washed with saturated aqueous NaCl solution (3×)
  6. dry with materialThe organic layer is dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by reverse phase prep-HPLC (Waters)

Sources & evidence

ORD record
ord-2d5d7f9b586a4754b12224745d4a990d
Source dataset
uspto-grants-2013_04
Patent number
US08420657B2

Reaction notes

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