HCID 178440277, compound → HCID 178440274, compound

HRID 411580Notes

Reaction equation

HRID 411580 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N:27](C(OC(C)(C)C)=O)[C:28](=[O:34])[C@@H:29]4[CH2:33][CH2:32][CH2:31][NH:30]4)=[CH:23][CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:42]([CH3:44])[CH3:43])[NH:11]1>Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH:27][C:28](=[O:34])[C@@H:29]4[CH2:33][CH2:32][CH2:31][NH:30]4)=[CH:25][CH:26]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:42]([CH3:44])[CH3:43])[NH:11]1

Participants

3

Reactant 1

HCID 178440277HCID 178440277, compound

Product 1

HCID 178440274HCID 178440274, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Fifty mg (0.076 mmol) of (S)-1-(2,4,6-trichloro phenyl)-3-isopropyl-6-(4-(N-t-butoxycarbonylprolinamido)benzyl)pyrazolo[3,4-d]pyrimidin-4-one was dissolved in 2 mL of 4 M HCl, and the solution was stirred 1 h at RT. The solution was concentrated under reduced pressure to afford 45 mg (100%) of (S)-1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(prolinamido)benzyl)pyrazolo[3,4-d]pyrimidin-4-one as a white, amorphous solid. 1H NMR (300 MHz, DMSO) δ 12.42(s, 1H); 10.67(s, 1H); 7.97(s, 2H); 7.49(d, 2H, J=8.5 Hz); 7.23(d, 2H, J=8.4 Hz); 4.27-4.31(m, 1H); 3.82(s, 2H); 3.18-3.34(m, 5H); 2.28-2.40(m, 1H); 1.84-1.95(m, 3H); 1.28(d, 6H, J=6.9 Hz).

Workup

  1. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c921a18a94654f928ca6c9e6664b1713
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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