5-chloro-N-(2-(isopropylsulfonyl)phenyl)-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine → HCID 178428330, compound

HRID 2046997Notes

Reaction equation

HRID 2046997 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[C:5]2[N:10]=[N:9][N:8](CC3C=CC(OC)=CC=3)[C:6]=2[N:7]=1.[CH:33]([O:36][C:37]1[CH:43]=[C:42]([CH:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[C:41]([CH3:50])=[CH:40][C:38]=1[NH2:39])([CH3:35])[CH3:34]>Cl.O1CCOCC1>[CH:33]([O:36][C:37]1[CH:43]=[C:42]([CH:44]2[CH2:45][CH2:46][NH:47][CH2:48][CH2:49]2)[C:41]([CH3:50])=[CH:40][C:38]=1[NH:39][C:2]1[N:3]=[C:4]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[S:27]([CH:30]([CH3:31])[CH3:32])(=[O:28])=[O:29])[C:5]2[N:10]=[N:9][NH:8][C:6]=2[N:7]=1)([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 582908585-chloro-N-(2-(isopropylsulfonyl)phenyl)-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amineHCID 582908952-Isopropoxy-5-methyl-4-(piperidin-4-yl)aniline

Product 1

HCID 178428330HCID 178428330, compound

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 5-chloro-N-(2-(isopropylsulfonyl)phenyl)-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine (10 mg) and 2-isopropoxy-5-methyl-4-(piperidin-4-yl)aniline (7 mg) in 2 M HCl/dioxane (2 mL) was sealed in a pressure tube and heated at 110° C. for 2 days. It was cooled to room temperature and solvent was removed under reduced pressure. The remaining residue was dissolved in trifluoroacetic acid (2 mL) and heated to 80° C. for 2 h. Trifluoroacetic acid was removed and the remaining product was purified by preparative LC-MS to afford desired product. 1H NMR (400 MHz, MeOD-d4) δ 8.67 (d, 1H), 7.98 (m, 2H), 7.74 (t, 1H), 7.43 (t, 1H), 6.82 (s, 1H), 4.61 (m, 1H), 3.57 (m, 2H), 3.38 (m, 1H), 3.18-3.24 (m, 2), 2.26 (s, 3H), 2.03 (m, 2H), 1.82-1.93 (m, 2H), 1.41 (d, 6H), 1.31 (d, 6H) ppm; ESMS calculated for C28H36N8O3S (m/z): 564.2 (M+H+), found: 565.2.

Workup

  1. temperatureIt was cooled to room temperature
  2. customsolvent was removed under reduced pressure
  3. dissolutionThe remaining residue was dissolved in trifluoroacetic acid (2 mL)
  4. temperatureheated to 80° C. for 2 h
  5. customTrifluoroacetic acid was removed
  6. customthe remaining product was purified by preparative LC-MS

Sources & evidence

ORD record
ord-229119a86c4c4301bf35b482e22f4251
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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