Ethyl Acetate → 8-[[5-Chloro-2-[[1-(2-hydroxyethyl)-3-methyl-pyrazol-4-yl]amino]-4-pyridyl]amino]-2-methyl-3,4-dihydroisoquinolin-1-one

HRID 1045968Notes

Reaction equation

HRID 1045968 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[C:17](=[O:19])[N:16]([CH3:20])[CH2:15][CH2:14]3)[C:5]([Cl:21])=[CH:4][N:3]=1.[NH2:22][C:23]1[C:24]([CH3:31])=[N:25][N:26]([CH2:28][CH2:29][OH:30])[CH:27]=1.CCOC(C)=O>CO>[Cl:21][C:5]1[C:6]([NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[C:17](=[O:19])[N:16]([CH3:20])[CH2:15][CH2:14]3)=[CH:7][C:2]([NH:22][C:23]2[C:24]([CH3:31])=[N:25][N:26]([CH2:28][CH2:29][OH:30])[CH:27]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 552846902-(4-Amino-3-methyl-pyrazol-1-yl)-ethanolHCID 866551378-[(2,5-Dichloropyridin-4-yl)amino]-2-methyl-3,4-dihydroisoquinolin-1-one

Product 1

HCID 583365938-[[5-Chloro-2-[[1-(2-hydroxyethyl)-3-methyl-pyrazol-4-yl]amino]-4-pyridyl]amino]-2-methyl-3,4-dihydroisoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

This compound was prepared from 8-[(2,5-dichloropyridin-4-yl)amino]-2-methyl-3,4-dihydroisoquinolin-1-one and 2-(4-amino-3-methyl-pyrazol-1-yl)ethanol. Column chromatography (SiO2, 50 equiv.; 95:5; EtOAc:MeOH) followed by prep. TLC (SiO2: 20×20 cm; 1000 μM, Analtech, EtOAc:MeOH; 95:5) furnished 45 mg of the desired compound. 1H NMR spectrum (CDCl3) 2.09 (s, 3H), 2.91 (t, 2H), 3.11 (s, 3H), 3.25 (bs, 1H), 3.51 (t, 2H), 3.86-3.95 (m, 2H), 4.05-4.10 (m, 2H), 5.89 (s, 1H), 6.44 (s, 1H), 6.68 (d, 1H), 7.14-7.29 (m, 2H), 7.44 (s, 1H), 7.88 (s, 1H), 11.09 (s, 1H); Mass spectrum: ESI+ MH+ 427

Sources & evidence

ORD record
ord-32ba88885471467fa5ec3b1e8afa3e8b
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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