5-Bromopyridine-2,3-diamine → HCID 178463876, compound

HRID 2218431Notes

Reaction equation

HRID 2218431 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10]([N:12]([CH2:20][CH3:21])[C:13]1[S:14][C:15]([CH:18]=O)=[CH:16][N:17]=1)[CH3:11]>CN1C(=O)CCC1.[N+](C1C=CC=CC=1)([O-])=O.CC#N.O>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]=[C:18]([C:15]3[S:14][C:13]([N:12]([CH2:10][CH3:11])[CH2:20][CH3:21])=[N:17][CH:16]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 6911565-Bromopyridine-2,3-diamineHCID 27854122-(diethylamino)-1,3-thiazole-5-carbaldehyde

Product 1

HCID 178463876HCID 178463876, compoundYield 6%

Reagents, catalysts & solvents 3

HCID 7416NitrobenzeneSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
170 °C

Procedure

5-Bromopyridine-2,3-diamine (0.1 g, 0.53 mmol) was dissolved in NMP (0.5 ml) and heated to 170° C. 2-(Diethylamino)-1,3-thiazole-5-carbaldehyde (0.098 g, 0.53 mmol) dissolved in nitrobenzene (1.0 ml) was added slowly (20 min). After 2 h, the reaction mixture was diluted with CH3CN/water and purified by HPLC-C18, giving the title product (0.01 g, 6%).

Workup

  1. additionwas added slowly (20 min)
  2. custompurified by HPLC-C18

Sources & evidence

ORD record
ord-6b0253c02e794850893631dfca338353
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

Loading…