m-Chloroperbenzoic acid → 1-[5-Isopropyl-4-(1H-pyrrolo[2,3-b]pyridin-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-6-yloxy]-propan-2-ol

HRID 1064253Notes

Reaction equation

HRID 1064253 reaction equation
[CH:1]([C:4]1[C:5]([O:15][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:6][N:7]2[C:12]=1[C:11](SC)=[N:10][CH:9]=[N:8]2)([CH3:3])[CH3:2].C([Si](C(C)C)(C(C)C)[N:24]1[C:28]2=[N:29][CH:30]=[C:31]([NH2:33])[CH:32]=[C:27]2[CH:26]=[CH:25]1)(C)C.ClC1C=CC=C(C(OO)=O)C=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)(Cl)Cl.C1COCC1>[CH:1]([C:4]1[C:5]([O:15][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:6][N:7]2[C:12]=1[C:11]([NH:33][C:31]1[CH:32]=[C:27]3[CH:26]=[CH:25][NH:24][C:28]3=[N:29][CH:30]=1)=[N:10][CH:9]=[N:8]2)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 222736141-[Tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-amineHCID 222736261-(5-Isopropyl-4-methylsulfanylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-propan-2-ol

Product 1

HCID 222736641-[5-Isopropyl-4-(1H-pyrrolo[2,3-b]pyridin-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-6-yloxy]-propan-2-olYield 1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

1-(5-Isopropyl-4-methylsulfanylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-propan-2-ol (262 mg, 0.93 mmol, obtained from Example 25 using procedure in Step B of Example 7) and 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-ylamine (290 mg, 0.93 mmol) were dissolved in chloroform and m-chloroperbenzoic acid (60%, 535 mg, 1.86 mmol) was added. The mixture was heated at 120° C. for 10 min in a Personal Chemistry Smith Enrys Optimizer™ microwave oven. The solution was evaporated in vacuo and the residue was purified by preparative HPLC. The isolated product was dissolved in of THF (10 mL) and TBAF (1.0 M, 0.2 mL, 0.2 mmol) was added. The mixture was stirred for 5 min. and the solvent was evaporated in vacuo. The residue was purified by preparative HPLC to afford the title compound (3 mg, 1%).

Workup

  1. customThe solution was evaporated in vacuo
  2. customthe residue was purified by preparative HPLC
  3. additionwas added
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0aec2b7d11964268bdd963de1046b90f
Source dataset
uspto-grants-2005_11
Patent number
US06969717B2

Reaction notes

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