Water → HCID 59276196, compound

HRID 2070886Notes

Reaction equation

HRID 2070886 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.BrC1N2N=C(N[C:32]3[CH:39]=[CH:38][C:35](C#N)=[CH:34][CH:33]=3)N=C2C=CC=1.[OH2:40].[OH-].[Na+]>P(=O)(O)(O)O>[OH:40][C:32]1[CH:33]=[C:34]([C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12]4[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:35]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 86640816HCID 86640816, compoundHCID 86640817HCID 86640817, compound

Product 1

HCID 59276196HCID 59276196, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzamide. A pale yellow solution of 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzonitrile (0.909 g, 2.89 mmol) in 85% phosphoric acid (15 mL) was heated at 100° C. for 2 h. Upon completion of the reaction as indicated by LCMS the reaction mixture was poured into minimum water, and made neutral with 1N sodium hydroxide (pH 6-7). The mixture was extracted with 20% isopropanol in chloroform several times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by silica gel chromatography using a gradient of 0-8% of saturated methanolic ammonia in chloroform to give the title compound as a pale yellow solid (0.677 g, 71% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.20 (s, 1H), 7.84 (d, 2H, J=8 Hz), 7.78-7.75 (m, 3H), 7.66 (d, 1H, J=8 Hz), 7.53 (t, 1H, J=8 Hz), 7.7.45-7.42 (m, 1H), 7.16 (br s, 1H); MS (ESI) m/z 332.16 and 334.16 [M]+ and [M+2]+

Workup

  1. customUpon completion of the reaction
  2. extractionThe mixture was extracted with 20% isopropanol in chloroform several times
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6b44ee7785b247d4a64baeba47983961
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

Loading…