HCID 90386419, compound → HCID 178514684, compound

HRID 2170164Notes

Reaction equation

HRID 2170164 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]=[C:26]([S:40]([NH:43]C(C)(C)C)(=[O:42])=[O:41])[C:27]([O:30]CC3C=CC(OC)=CC=3)=[N:28][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:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]2[CH:25]=[C:26]([S:40]([NH2:43])(=[O:42])=[O:41])[C:27]([OH:30])=[N:28][CH:29]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 90386419HCID 90386419, compound

Product 1

HCID 178514684HCID 178514684, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

5-(4-(Benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)-N-(tert-butyl)-2-((4-methoxybenzyl)oxy)pyridine-3-sulfonamide (0.100 g, 0.154 mmol) was dissolved in TFA (25 mL) and stirred for 6 h at 60° C. TFA was removed under reduced pressure and 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 give a residue which was purified by preparative HPLC (Condition B-70 as described in general methods) to get 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)-2-hydroxypyridine-3-sulfonamide (20.0 mg, 27.5%). LCMS Condition B-38: retention time 2.48 min, [M−1]=471.0. HPLC Condition B-6: retention time 15.64 min, Purity 99.67%. 1H NMR (400 MHz, DMSO-d6) δ 4.75 (d, J=8.0 Hz, 2H), 6.61 (t, J=8.0 Hz, 1H), 6.74 (d, J=4.0 Hz, 1H), 7.03 (s, 2H), 7.24-7.28 (m, 1H), 7.32-7.39 (m, 5H), 7.44-7.52 (m, 4H), 7.87 (d, J=2.8 Hz, 1H), 8.42 (d, J=4.0 Hz, 1H), 8.77 (d, J=4.0 Hz, 1H), 12.70 (s, 1H).

Workup

  1. customTFA was removed under reduced pressure and reaction mixture
  2. additionwas 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
  7. customto give a residue which
  8. customwas purified by preparative HPLC (Condition B-70 as described in general methods)

Sources & evidence

ORD record
ord-759774fb02d249a18bd64fc5c58b894f
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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