Hydrazine, cyclopropyl-, hydrochloride (1:1) → 4-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-ethyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873922Notes

Reaction equation

HRID 873922 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)[CH:9]2[C:26](=O)[CH2:27][CH3:28])=[CH:4][CH:3]=1.Cl.[CH:31]1([NH:34][NH2:35])[CH2:33][CH2:32]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:9]3[C:26]([CH2:27][CH3:28])=[N:35][N:34]([CH:31]4[CH2:33][CH2:32]4)[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:4][CH:3]=1

Participants

3

Reactant 2

HCID 19594967Hydrazine, cyclopropyl-, hydrochloride (1:1)HCID 1177025355-(4-Chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-propionylpyrrolidine-2,3-dione

Product 1

HCID 918263154-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-ethyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

Procedure

The title compound was prepared in analogy to the procedure described for Example 68 using 5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-propionylpyrrolidine-2,3-dione (Step 70.1) and cyclopropylhydrazine hydrochloride. Further purification by preparative achiral SFC (4-ethyl-pyridine, gradient 13-18% in 6 min_total 11 min) to afford the title product as colorless foam. tR: 1.02 min (LC-MS 2); ESI-MS: 447 [M+H]+ (LC-MS 2); Rf=0.36 (EtOAc/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.91 (t, J=7.6 Hz, 3H) 1.03-1.11 (m, 2H) 1.21-1.32 (m, 2H) 2.29 (dt, J=15.0, 7.6 Hz, 1H) 2.38 (dt, J=15.1, 7.7 Hz, 1H) 2.45 (s, 3H) 2.64 (s, 3H) 3.85 (tt, J=7.4, 3.8 Hz, 1H) 6.48 (s, 1H) 7.28-7.42 (m, 5H) 8.45 (s, 1H).

Workup

  1. customThe title compound was prepared in analogy to the procedure
  2. customFurther purification by preparative achiral SFC (4-ethyl-pyridine, gradient 13-18% in 6 min_total 11 min)

Sources & evidence

ORD record
ord-dfc06b7202ad458fbeacd5a217dd6e04
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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