Iodo benzene diacetate → Methyl 4-{3-[1-(1,3-benzothiazol-6-yl)cyclopropyl][1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl}benzoate

HRID 1099064Notes

Reaction equation

HRID 1099064 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]3([CH:13]=O)[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:15]([C:17]1[N:18]=[N:19][C:20]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)=[CH:21][N:22]=1)[NH2:16].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C.C(O)(=O)C>[S:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]4[N:18]5[N:19]=[C:20]([C:23]6[CH:24]=[CH:25][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:31][CH:32]=6)[CH:21]=[N:22][C:17]5=[N:15][N:16]=4)[CH2:11][CH2:12]3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 12217721Iodo benzene diacetateHCID 59216328Methyl 4-(3-hydrazino-1,2,4-triazin-6-yl)benzoateHCID 823968391-(1,3-Benzothiazol-6-yl)cyclopropanecarbaldehyde

Product 1

HCID 66813212Methyl 4-{3-[1-(1,3-benzothiazol-6-yl)cyclopropyl][1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl}benzoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 1-(1,3-benzothiazol-6-yl)cyclopropanecarbaldehyde (80.0 mg, 0.39 mmol) and methyl 4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate (96.5 mg, 0.394 mol) in ethanol (2.7 mL) and acetic acid (0.53 mL) was stirred at RT for 3 h. The mixture was concentrated. The residue was dissolved in DCM (5 mL), followed by addition iodobenzene diacetate (150 mg, 0.47 mmol). The mixture was stirred at RT for 6 h, and quenched with saturated sodium bicarbonate (25 mL). The mixture was extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was flash chromatographed on a silica gel column with 40% ethyl acetate in DCM to afford the desired product. Analytical LCMS: (M+H)+=429.0.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in DCM (5 mL)
  3. stirringThe mixture was stirred at RT for 6 h
  4. customquenched with saturated sodium bicarbonate (25 mL)
  5. extractionThe mixture was extracted with ethyl acetate (3×40 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customchromatographed on a silica gel column with 40% ethyl acetate in DCM

Sources & evidence

ORD record
ord-21f6a090996c415299f1246d6b2cf198
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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