1H-Imidazole-4-carbaldehyde → HCID 178473725, compound

HRID 849431Notes

Reaction equation

HRID 849431 reaction equation
[ClH:1].Cl.Cl.[NH:4]1[CH:8]=[C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]4[CH:22]=N[CH:24]=[CH:25][CH:26]=4)=[CH:20][C:15]=3[CH2:14][N:13]([C:27](=[O:32])[C:28](F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)[N:6]=[CH:5]1.N1C=C(C=O)N=[CH:41]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(O)(=O)C>[ClH:1].[C:27]([N:13]1[CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:22]=[CH:41][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:16]=2[N:10]([CH2:9][C:7]2[N:6]=[CH:5][NH:4][CH:8]=2)[CH2:11][C@H:12]1[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:32])[CH3:28]

Participants

6

Reactant 3

HCID 764281H-Imidazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178478619HCID 178478619, compound

Product 1

HCID 178473725HCID 178473725, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 115 mg (0.29 mmol) of Compound B in 2.5 mL of dichloroethane and 2.5 mL of glacial acetic acid was treated with 69 mg (0.71 mmol) of 4-imidazole-carboxaldehyde, 3A sieves and stirred at rt for 18 hrs. The mixture was treated with 122 mg (0.58 mmol) of sodium triacetoxyborohydride in one portion and stirred at rt for 30 min and filtered. The filtrate was partitioned between 100 mL of ethyl acetate and 100 mL of 1 N sodium hydroxide. The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The oil was purified by reverse phase preparative HPLC (gradient of aq methanol with 0.1% TFA). The yellow foam was evaporated 3× from methanolic hydrogen chloride. The foam was dissolved in water and lyophilyzed to afford 30 mg (22%) of Compound C as a yellow lyophilate. MS: (M+H)+ =480.

Workup

  1. stirringstirred at rt for 30 min
  2. filtrationfiltered
  3. customThe filtrate was partitioned between 100 mL of ethyl acetate and 100 mL of 1 N sodium hydroxide
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe oil was purified by reverse phase preparative HPLC (gradient of aq methanol with 0.1% TFA)
  8. customThe yellow foam was evaporated 3× from methanolic hydrogen chloride
  9. dissolutionThe foam was dissolved in water

Sources & evidence

ORD record
ord-6020438c9bbd437e832f1c6384ce9826
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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