Hydrazine hydrate (1:1) → HCID 178428082, compound

HRID 873987Notes

Reaction equation

HRID 873987 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:14]=[C:15]([CH3:23])[C:16]4[N:17]([C:19]([CH3:22])=[N:20][N:21]=4)[CH:18]=3)[C:11](=[O:24])[C:10](O)=[C:9]2[C:26]([CH:28]2[CH2:30][CH2:29]2)=O)=[CH:4][CH:3]=1.O.[NH2:32][NH2:33]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:9]3[C:26]([CH:28]4[CH2:30][CH2:29]4)=[N:33][NH:32][C:10]=3[C:11](=[O:24])[N:12]2[C:13]2[CH:14]=[C:15]([CH3:23])[C:16]3[N:17]([C:19]([CH3:22])=[N:20][N:21]=3)[CH:18]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1177026275-(4-chlorophenyl)-4-(cyclopropanecarbonyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]-pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

Product 1

HCID 178428082HCID 178428082, compound

Procedure

The title compound was prepared in analogy to the procedure described in Example 57 using 5-(4-chlorophenyl)-4-(cyclopropanecarbonyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one (Step 117.1) and hydrazine hydrate. The crude product was purified by silica gel column chromatography (7.5% MeOH/CH2Cl2). tR: 0.83 min (LC-MS 2); ESI-MS: 419 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.00-0.11 (m, 1H) 0.44-0.65 (m, 1H) 0.65-0.78 (m, 1H) 0.80-0.90 (m, 1H) 1.68-1.88 (m, 1H) 2.42 (s, 3H) 2.61 (s, 3H) 6.44 (s, 1H) 7.16-7.45 (m, 5H) 8.38 (d, J=0.8 Hz, 1H) 13.55 (br. s., 1H).

Workup

  1. customThe crude product was purified by silica gel column chromatography (7.5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a051652fde114143bcb04c1482416312
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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