5-Chloromethyloxazolidin-2-one → HCID 67298101, compound

HRID 1520396Notes

Reaction equation

HRID 1520396 reaction equation
Cl[CH2:2][CH:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1.[CH3:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[CH:19]=2)[N:14]=[C:13]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[N:12]=1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC>CN1C(=O)CCC1.CO>[CH3:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]3[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=3)[O:27][CH2:2][CH:3]3[O:7][C:6](=[O:8])[NH:5][CH2:4]3)[CH:19]=2)[N:14]=[C:13]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[N:12]=1

Participants

6

Reactant 3

HCID 908155-Chloromethyloxazolidin-2-oneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 67297993HCID 67297993, compound

Product 1

HCID 67298101HCID 67298101, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To 5-(chloromethyl)oxazolidin-2-one (45 μmol) was added the solution of 3-(4-(methylamino)-2-(pyridin-3-yl)quinazolin-6-yl)phenol (30 μmol) in NMP (200 μL). PS-BEMP (90 μmol) was added to the vials by resin dispenser. After the reaction mixture was heated at 90° C. for 12 h, the residue was diluted with methanol and purified by PREP-HPLC Condition D. The target fraction was lyophilized to afford the titled compound whose structure was finally confirmed by LCMS using LCMS Method E.

Workup

  1. custompurified by PREP-HPLC Condition D

Sources & evidence

ORD record
ord-94e609f8406b48db9ca1eaa19705cdd6
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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