N-(tert-Butyl)-2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide → 2-Isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide

HRID 2170194Notes

Reaction equation

HRID 2170194 reaction equation
C([NH:5][S:6]([C:9]1[C:10]([O:38][CH:39]([CH3:41])[CH3:40])=[N:11][CH:12]=[C:13]([C:15]2[N:20]=[C:19]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[C:18]3=[C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:30]=[CH:31][N:17]3[N:16]=2)[CH:14]=1)(=[O:8])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[CH:39]([O:38][C:10]1[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:14][C:13]([C:15]2[N:20]=[C:19]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[C:18]3=[C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:30]=[CH:31][N:17]3[N:16]=2)=[CH:12][N:11]=1)([CH3:41])[CH3:40]

Participants

3

Reactant 1

HCID 90386266N-(tert-Butyl)-2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide

Product 1

HCID 903861322-Isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamideYield 41.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(tert-Butyl)-2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (0.175 g, 0.306 mmol) in TFA (30 mL) was stirred at RT for 12 h. TFA was removed under reduced pressure and reaction mixture was diluted with 10% NaHCO3 (50 mL). The reaction mixture was extracted with EtOAc (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a residue which was purified by preparative HPLC (Condition B-99 as described in general methods) to afford 2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (65.0 mg, 40.8%) as a white solid. LCMS Condition B-39: retention time 2.32 min, [M+1]=516.2. HPLC Condition B-5: retention time 8.21 min, purity 99.29%. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (d, J=7.1 Hz, 6H), 4.88 (d, J=4.5 Hz, 2H), 5.14 (quintet, J=6.8 Hz, 1H), 6.77 (d, J=3.1 Hz, 1H), 7.08 (s, 2H), 7.24-7.31 (m, 2H), 7.42-7.49 (m, 2H), 7.50-7.62 (m, 4H), 7.77 (td, J=7.7 Hz, J=1.8 Hz, 1H), 7.90 (d, J=2.5 Hz, 1H), 8.42 (dt, J=5.1 Hz, J=1.2 Hz, 1H), 8.65 (d, J=2.5 Hz, 1H), 8.73 (d, J=2.5 Hz, 1H).

Workup

  1. customTFA was removed under reduced pressure and reaction mixture
  2. additionwas diluted with 10% NaHCO3 (50 mL)
  3. extractionThe reaction mixture was extracted with EtOAc (3×30 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue which
  8. customwas purified by preparative HPLC (Condition B-99 as described in general methods)

Sources & evidence

ORD record
ord-ad8a648662f3435f99041d84293d7d54
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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