1-Isopropylhydrazine hydrochloride → 5-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-(4-chlorophenyl)-2-isopropyl-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(2H)-one

HRID 873914Notes

Reaction equation

HRID 873914 reaction equation
[C:1]([C:4]1[CH:5]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:6]([C:11]2[CH:12]=[C:13]([Cl:19])[C:14](=[O:18])[N:15]([CH3:17])[CH:16]=2)[C:7](=[O:10])[C:8]=1O)(=O)[CH3:2].Cl.[CH:28]([NH:31][NH2:32])([CH3:30])[CH3:29]>>[Cl:19][C:13]1[C:14](=[O:18])[N:15]([CH3:17])[CH:16]=[C:11]([N:6]2[CH:5]([C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[C:4]3[C:8](=[N:32][N:31]([CH:28]([CH3:30])[CH3:29])[C:1]=3[CH3:2])[C:7]2=[O:10])[CH:12]=1

Participants

3

Reactant 2

HCID 855731-Isopropylhydrazine hydrochlorideHCID 1177027635-(3-acetyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3-chloro-1-methyl-pyridin-2(1H)-one

Product 1

HCID 862923845-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-(4-chlorophenyl)-2-isopropyl-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(2H)-one

Procedure

The title compound was prepared in analogy to the procedure described in Example 58 using 5-(3-acetyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3-chloro-1-methyl-pyridin-2(1H)-one (Step 58.1) and isopropylhydrazine hydrochloride. The crude material was purified by preparative achiral SFC (column 4-Ethyl-pyridine, gradient 17-22% in 6 min_total 11 min). tR: 4.45 min (HPLC 1); tR: 1.01 min (LC-MS 2); ESI-MS: 431 [M+H]+ (LC-MS 2); Rf=0.31 (EtOAc); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34-1.42 (m, 6H) 2.07 (s, 3H) 3.43 (s, 3H) 4.52-4.62 (m, 1H) 6.12 (s, 1H) 7.23-7.30 (m, 2H) 7.34-7.40 (m, 2H) 7.87-7.90 (m, 1H) 7.90-7.93 (m, 1H).

Workup

  1. customThe crude material was purified by preparative achiral SFC (column 4-Ethyl-pyridine, gradient 17-22% in 6 min_total 11 min)

Sources & evidence

ORD record
ord-192b66cc695d42b38b910350400d7016
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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