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

HRID 1478402Notes

Reaction equation

HRID 1478402 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2[N:20]3[CH:21]=[CH:22][C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:19]3[C:18](Cl)=[N:17][N:16]=2)[CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCOCC1>[CH2:31]([NH:38][C:18]1[C:19]2[N:20]([CH:21]=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]([C:13]2[CH:14]=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])[CH:10]=[N:11][CH:12]=2)=[N:16][N:17]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 90425182N-(tert-butyl)-5-(1-chloro-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)pyridine-3-sulfonamide

Product 1

HCID 904243205-(1-(benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)-N-(tert-butyl)pyridine-3-sulfonamideYield 129.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(tert-butyl)-5-(1-chloro-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)pyridine-3-sulfonamide (0.100 g, 0.226 mmol) in 1,4-dioxane (10 mL) was added benzylamine (0.124 mL, 1.13 mmol) at room temperature. The resulting reaction mixture was heated at 100° C. for 12 h in a sealed tube. The reaction mixture was diluted with ice cold water (150 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give a residue which was purified by silica gel column chromatography using CombiFlash (REDISEP®, silica gel, 12 g, 50% EtOAc/hexanes) to yield 5-(1-(benzylamino)-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)-N-(tert-butyl)pyridine-3-sulfonamide (0.150 g, 33.0%). LCMS Method B-4: retention time 1.15 min, [M+1]=513.43. 1H NMR (400 MHz, DMSO-d6) δ ppm: 1.17 (s, 9H), 4.31 (d, J=5.2 Hz, 2H), 5.65 (t, J=5.2 Hz, 1H), 6.96 (d, J=2.8 Hz, 1H), 7.22-7.35 (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, 1H), 8.65 (t, J=2.0 Hz, 1H), 9.12 (d, J=2.0 Hz, 1H), 9.34 (d, J=2.0 Hz, 1H).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a residue which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-982b5e9868184563934b1eff60508413
Source dataset
uspto-grants-2016_08
Patent number
US09403834B2

Reaction notes

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