Hydrazine hydrate (1:1) → HCID 178434164, compound

HRID 873957Notes

Reaction equation

HRID 873957 reaction equation
[C:1]([C:4]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:7]([C:16]2[CH:17]=[C:18]([CH3:26])[C:19]3[N:20]([C:22]([CH3:25])=[N:23][N:24]=3)[CH:21]=2)[C:6](=[O:27])[C:5]=1O)(=O)[CH3:2].O.[NH2:30][NH2:31]>>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]2[C:4]3[C:1]([CH3:2])=[N:31][NH:30][C:5]=3[C:6](=[O:27])[N:7]2[C:16]2[CH:17]=[C:18]([CH3:26])[C:19]3[N:20]([C:22]([CH3:25])=[N:23][N:24]=3)[CH:21]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1177026714-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

Product 1

HCID 178434164HCID 178434164, compound

Procedure

The title compound was prepared in analogy to the procedure described in Example 57 using 4-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one (Step 90.1) and hydrazine hydrate. The crude material was purified by silica gel column chromatography (7.5% MeOH/CH2Cl2) and triturated in Et2O. tR: 0.75 min (LC-MS 2); ESI-MS: 393 [M+H]+ (LC-MS 2); Rf=0.23 (7.5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.08 (s, 3H) 2.46 (s, 3H) 2.64 (s, 3H) 6.48 (s, 1H) 7.19-7.46 (m, 5H) 8.47 (s, 1H) 13.49 (br. s., 1H).

Workup

  1. customThe crude material was purified by silica gel column chromatography (7.5% MeOH/CH2Cl2)
  2. customtriturated in Et2O

Sources & evidence

ORD record
ord-592fc86d2c50402ca74e6159ca411c3a
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…