1423034-21-2 → HCID 86292968, compound

HRID 873963Notes

Reaction equation

HRID 873963 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]([O:23][CH3:24])[C:16]4[N:17]([C:19]([CH3:22])=[N:20][N:21]=4)[CH:18]=3)[C:11](=[O:25])[C:10](=O)[CH:9]2[C:27](=O)[CH2:28][CH3:29])=[CH:4][CH:3]=1.Cl.[F:32][C:33]([F:41])([F:40])[CH2:34][O:35][CH2:36][CH2:37][NH:38][NH2:39]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:9]3[C:27]([CH2:28][CH3:29])=[N:39][N:38]([CH2:37][CH2:36][O:35][CH2:34][C:33]([F:41])([F:40])[F:32])[C:10]=3[C:11](=[O:25])[N:12]2[C:13]2[CH:14]=[C:15]([O:23][CH3:24])[C:16]3[N:17]([C:19]([CH3:22])=[N:20][N:21]=3)[CH:18]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1177029431423034-21-2HCID 117702964HCID 117702964, compound

Product 1

HCID 86292968HCID 86292968, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The tile compound was prepared in analogy to the procedure described in Example 68 using 5-(4-chlorophenyl)-1-(8-methoxy-3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-propionylpyrrolidine-2,3-dione (Step 84.5) and (2-(2,2,2-trifluoroethoxy)ethyl)hydrazine hydrochloride in MeOH and TEA. The crude material was first purified by silica gel chromatography (hexane/EtOAc/MeOH 75:25:5 to 5:1) followed by preparative achiral SFC (Propyl-pyridyl-urea, gradient 13-18% in 6 min_total 11 min). tR: 1.04 min (LC-MS 2); ESI-MS: 549 [M+H]+ (LC-MS 2).

Workup

  1. customThe tile compound was prepared in analogy to the procedure
  2. customThe crude material was first purified by silica gel chromatography (hexane/EtOAc/MeOH 75:25:5 to 5:1)
  3. customfollowed by preparative achiral SFC (Propyl-pyridyl-urea, gradient 13-18% in 6 min_total 11 min)

Sources & evidence

ORD record
ord-624a9e6e010c4733a9cb727388e505a4
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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