Hydrochloric Acid → HCID 58089004, compound

HRID 1959533Notes

Reaction equation

HRID 1959533 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.C1([Mg]Cl)CCCCC1.[NH2:17][C:18]1[N:22]([C:23]2[CH:24]=[C:25]([CH:32]=[CH:33][C:34]=2[CH3:35])[C:26]([NH:28][CH:29]2[CH2:31][CH2:30]2)=[O:27])[CH:21]=[N:20][C:19]=1[C:36]#N.Cl.C([O-])([O-])=[O:40].[K+].[K+]>C1COCC1>[NH2:17][C:18]1[N:22]([C:23]2[CH:24]=[C:25]([CH:32]=[CH:33][C:34]=2[CH3:35])[C:26]([NH:28][CH:29]2[CH2:31][CH2:30]2)=[O:27])[CH:21]=[N:20][C:19]=1[C:36](=[O:40])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 58088961HCID 58088961, compoundHCID 178478990HCID 178478990, compound

Product 1

HCID 58089004HCID 58089004, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-1-iodobenzene (2.82 g) in THF (20 mL) at −40° C. under N2 was added cyclohexylmagnesium chloride (2M in THF, 6 mL). The solution was kept at −40° C. to 0° C. for 20 min. then 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide (0.18 g) was added and the reaction was kept at rt for 1 h. Then HCl (4 M, 20 mL) was added and the mixture was kept at rt for two days. The mixture was neutralized with K2CO3 solution and extracted with EtOAc (2×100 mL) and the combined organics dried over Na2SO4, and concentrated. Purification of the crude product by column chromatography (EtOAc) gave the desired product (0.15 g, 54%). HPLC (4 minute 10-90 gradient) tR1.85 min; MS m/z 438.10, 441.07 [M+H]+.

Workup

  1. waitthe reaction was kept at rt for 1 h
  2. waitthe mixture was kept at rt for two days
  3. extractionextracted with EtOAc (2×100 mL)
  4. dry with materialthe combined organics dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification of the crude product by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-4d0bdd2c1d27431590478cbe2ace4be0
Source dataset
uspto-grants-2013_04
Patent number
US08410160B2

Reaction notes

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