Hydrogen Peroxide → HCID 178513661, compound

HRID 2070889Notes

Reaction equation

HRID 2070889 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:34]=[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([NH:19][C@@H:20]4[CH2:25][CH2:24][C@H:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22][CH2:21]4)[N:13]3[N:12]=2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].C(C1C=CC(NC2N=C3C=CC=C(N[C@@H]4CC[C@H](NC(=O)OC(C)(C)C)CC4)N3N=2)=CC=1)#N.C(=O)([O-])[O-].[Na+].[Na+].OO>C(O)C.[Cl-].[Na+].O>[NH2:26][C@@H:23]1[CH2:24][CH2:25][C@H:20]([NH:19][C:18]2[N:13]3[N:12]=[C:11]([NH:10][C:7]4[CH:6]=[CH:5][C:4]([C:1]([NH2:2])=[O:3])=[CH:9][CH:8]=4)[N:34]=[C:14]3[CH:15]=[CH:16][CH:17]=2)[CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 178453995HCID 178453995, compoundHCID 178453996HCID 178453996, compound

Product 1

HCID 178513661HCID 178513661, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butyl cis-4-(2-(4-carbamoylphenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)cyclohexylcarbamate. To a pale yellow solution of tert-butyl cis-4-(2-(4-cyanophenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)cyclohexylcarbamate (0.078 g, 0.174 mmol) in ethanol (10 mL) (heated with a heat gun to get the starting material in solution) was added 3 N sodium carbonate (4 mL) and 30% w/w hydrogen peroxide (4 mL) at room temperature. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction as indicated by LCMS, the reaction mixture was poured into brine, and extracted with ethyl acetate several times. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by column chromatography (eluting with 0-10% saturated methanolic ammonia in chloroform) to give the title compound as a pale pink solid (0.066 g, 81% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 9.86 (s, 1H), 7.84 (d, 2H, J=8 Hz), 7.76 (d, 3H, J=8 Hz), 7.44 (t, 1H, J=8 Hz), 7.12 (s, 1H), 6.78 (d, 1H, J=8 Hz), 6.22 (d, 1H, J=8 Hz), 5.96 (d, 1H, J=8 Hz), 3.73-3.65 (m, 1H), 3.58-3.51 (m, 1H), 1.91-1.82 (m, 2H), 1.81-1.73 (m, 2H), 1.69-1.58 (m, 4H), 1.40 (s, 9H); MS (ESI) m/z 466.55 [M+1]+.

Workup

  1. customto get the starting material in solution)
  2. customUpon completion of the reaction
  3. extractionextracted with ethyl acetate several times
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude mixture was purified by column chromatography (eluting with 0-10% saturated methanolic ammonia in chloroform)

Sources & evidence

ORD record
ord-2fa30d713a504c82b41b188cf4e7f87b
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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