Iodine → HCID 24860658, compound

HRID 251346

Reaction equation

HRID 251346 reaction equation
Br[CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[Mg].II.[NH2:11][C:12]1[N:16]([C:17]2[CH:18]=[C:19]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:20]([NH:22][CH:23]2[CH2:25][CH2:24]2)=[O:21])[CH:15]=[N:14][C:13]=1[C:30]#N.C1C[O:35]CC1>>[NH2:11][C:12]1[N:16]([C:17]2[CH:18]=[C:19]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:20]([NH:22][CH:23]2[CH2:25][CH2:24]2)=[O:21])[CH:15]=[N:14][C:13]=1[C:30]([CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1)=[O:35]

Participants

6

Reactant 5

HCID 807IodineHCID 8028Tetrahydrofuran3×HCID 5462224MagnesiumHCID 133496544-BromotetrahydropyranHCID 58088961HCID 58088961, compound

Product 1

HCID 24860658HCID 24860658, compoundYield 30%

Procedure

A solution of 4-bromo-tetrahydro-pyran (0.82g, 5 mmol) in dry THF (10 mL) was added dropwise to the suspension of magnesium (132 mg, 5.5 mmol) and iodine (25 mg) in dry THF (20 mL) at 50° C. under N2. The mixture was stirred for 30 min after addition at 50° C., then cooled to room temperature. Then a THF (10 mL) solution of 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide (90 mg, 0.32 mmol) was added to the reaction mixture and it was stirred at room temperature for 3h then quenched with HCl (2N) and stirred at room temperature overnight. The pH of the solution was adjusted pH 8 with saturated aqueous K2CO3 was and it was extracted with EtOAc. The organic layer was washed by water and brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silical gel (EtOAc˜EtOAc:MeOH:Et3N=100:10:1), and the product was obtained as a beige solid (35 mg, 30%). HPLC (4 minute gradient) tR=3.05 min; MS m/z 369.18 [M+H]+.

Workup

  1. additionafter addition at 50° C.
  2. customthen quenched with HCl (2N)
  3. stirringstirred at room temperature overnight
  4. extractionit was extracted with EtOAc
  5. washThe organic layer was washed by water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography on silical gel (EtOAc˜EtOAc:MeOH:Et3N=100:10:1)

Sources & evidence

ORD record
ord-1cf12a8550e84eff861857800313f34d
Source dataset
uspto-grants-2011_01
Patent number
US07863314B2

Linked notes

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