3-Chloroaniline → HCID 21874542, compound

HRID 732984Notes

Reaction equation

HRID 732984 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]([OH:14])=O)[C:6]=2[N:7]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[Cl:32][C:33]1[CH:34]=[C:35]([CH:37]=[CH:38][CH:39]=1)[NH2:36]>CN(C=O)C.O>[NH2:1][C:2]1[N:3]=[C:4]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]([NH:36][C:35]3[CH:37]=[CH:38][CH:39]=[C:33]([Cl:32])[CH:34]=3)=[O:14])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 79323-ChloroanilineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 9813851HCID 9813851, compound

Product 1

HCID 21874542HCID 21874542, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of (5-amino-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)acetic acid (140 mg, 0.5 mmol) in DMF (1 mL) was treated with carbonyl diimidazole (81 mg, 0.5 mmol), stirred at room temperature for 1 h, treated with 3-chloroaniline (53 μL, 0.5 mmol) and the mixture heated to 50° C. for 16 h. The reaction mixture was cooled, diluted with water (3 mL) and filtered to give the title compound (94 mg, 48%) as a cream solid.

Workup

  1. temperaturethe mixture heated to 50° C. for 16 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-dd7136eefdd74b54a5f0f8b0198f814b
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

Loading…