Morpholine → HCID 86624992, compound

HRID 2099303Notes

Reaction equation

HRID 2099303 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][N:23]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:9]=[C:8]([CH2:19]Cl)[C:6]=2[N:7]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C(N(CC)C(C)C)(C)C>CS(C)=O>[F:16][C:15]([F:18])([F:17])[C:14]([OH:31])=[O:13].[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][N:23]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:9]=[C:8]([CH2:19][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 86624993HCID 86624993, compound

Product 1

HCID 86624992HCID 86624992, compoundYield 170.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-3-(chloromethyl)-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-1H-pyrazolo[4,3-d]pyrimidin-7-amine (300 mg, 0.7 mmol), morpholine (185 mg, 2.1 mmol) and N,N-diisopropylethylamine (270 mg, 2.1 mmol) were mixed in methyl sulfoxide (2 ml) in a reaction vial. The reaction mixture was stirred 18 hours at room temperature and then purified on reverse phase HPLC and lyophilized to give 5-chloro-3-(morpholin-4-ylmethyl)-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-1H-pyrazolo[4,3-d]pyrimidin-7-amine trifluoroacetate (350 mg).

Workup

  1. custompurified on reverse phase HPLC

Sources & evidence

ORD record
ord-686223a8ed8b4a36bc28a0efed50c50b
Source dataset
uspto-grants-2009_08
Patent number
US07569572B2

Reaction notes

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