5-(1-(benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)-N-(tert-butyl)pyridine-3-sulfonamide → 5-(1-(Benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)pyridine-3-sulfonamide

HRID 1478403Notes

Reaction equation

HRID 1478403 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]2[N:11]([CH:29]=[CH:30][C:31]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:12]([C:15]2[CH:16]=[C:17]([S:21]([NH:24]C(C)(C)C)(=[O:23])=[O:22])[CH:18]=[N:19][CH:20]=2)=[N:13][N:14]=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:10]2[N:11]([CH:29]=[CH:30][C:31]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:12]([C:15]2[CH:16]=[C:17]([S:21]([NH2:24])(=[O:22])=[O:23])[CH:18]=[N:19][CH:20]=2)=[N:13][N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 904243205-(1-(benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)-N-(tert-butyl)pyridine-3-sulfonamide

Product 1

HCID 904248145-(1-(Benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)pyridine-3-sulfonamideYield 45%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

5-(1-(Benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)-N-(tert-butyl)pyridine-3-sulfonamide (0.150 g, 0.293 mmol) was dissolved in TFA (10 mL) and stirred at 50° C. for 1 h. TFA was removed under reduced pressure and the resulting residue was diluted with saturated sodium bicarbonate (100 mL). The aqueous mixture was extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried over anhydrous sodium sulfate and evaporated under reduced pressure to give a residue which was purified by preparative HPLC (Condition B-5 described in general methods) to yield 5-(1-(benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)pyridine-3-sulfonamide (0.060 g, 45.0%) as a white solid. LCMS Method B-3: retention time 1.99 min, [M+1]=457.0. HPLC Method B-1: retention time 6.12 min, Purity 99.48%. 1H NMR (400 MHz, DMSO-d6) δ ppm: 4.67 (d, J=5.6 Hz, 2H), 5.64 (t, J=5.6 Hz, 1H), 6.97 (d, J=2.8 Hz, 1H), 7.25-7.35 (m, 5H), 7.42-7.44 (m, 1H), 7.47-7.50 (m, 2H), 7.55-7.57 (m, 2H), 7.69 (d, J=2.8 Hz, 1H), 7.75 (s, 2H), 8.63 (t, J=2.0 Hz, 1H), 9.16 (d, J=2.0 Hz, 1H), 9.24 (d, J=2.0 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-a76cf74b68b349e6a83cccf8e1e676d1
Source dataset
uspto-grants-2016_08
Patent number
US09403834B2

Reaction notes

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