HCID 90386097, compound → HCID 78324271, compound

HRID 2170161Notes

Reaction equation

HRID 2170161 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]2=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH:30]3[CH2:34][O:33]C(C)(C)[O:31]3)[CH:29]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[CH2:1]([NH:8][C:9]1[C:14]2=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]2[CH:29]=[C:28]([CH:30]([OH:31])[CH2:34][OH:33])[CH:27]=[N:26][CH:25]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 90386097HCID 90386097, compound

Product 1

HCID 78324271HCID 78324271, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

N-Benzyl-2-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.150 g, 0.314 mmol) was dissolved in TFA (10 mL) and stirred for 1 h at 60° C. TFA was removed under reduced pressure and the reaction mixture was diluted with saturated sodium bicarbonate (100 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried over sodium sulfate, filtered and evaporated under reduced pressure to a residue which was purified by preparative HPLC (Condition B-53 as described in general methods) to get 1-(5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)ethane-1,2-diol (90.0 mg, 65.5%). The enantiomers of 1-(5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)ethane-1,2-diol were separated by SFC (Condition B-52 as described in general methods).

Workup

  1. customTFA was removed under reduced pressure
  2. additionthe reaction mixture was diluted with saturated sodium bicarbonate (100 mL)
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure to a residue which
  7. customwas purified by preparative HPLC (Condition B-53 as described in general methods)

Sources & evidence

ORD record
ord-b27a77d0be1b433ab0645b6281d80220
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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