3-Hydroxyazetidine hydrochloride → HCID 86299225, compound

HRID 589141Notes

Reaction equation

HRID 589141 reaction equation
Cl[C:2]1[N:10]2[CH:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:12][O:13][C:8]3=[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[C:20]2[C:21]([CH3:26])=[N:22][O:23][C:24]=2[CH3:25])[N:3]=1.Cl.[NH:28]1[CH2:31][CH:30]([OH:32])[CH2:29]1>CO>[CH3:26][C:21]1[C:20]([C:7]2[C:8]3[O:13][CH2:12][CH:11]([C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)[N:10]4[C:2]([N:28]5[CH2:31][CH:30]([OH:32])[CH2:29]5)=[N:3][C:4]([C:9]=34)=[CH:5][CH:6]=2)=[C:24]([CH3:25])[O:23][N:22]=1

Participants

4

Reactant 2

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 90408846HCID 90408846, compound

Product 1

HCID 86299225HCID 86299225, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by methods analogous to Example 157, substituting 2-chloro-7-(3,5-dimethylisoxazol-4-yl)-4-pyridin-3-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazine, azetidin-3-ol hydrochloride and extending the reaction time to 60 min. The mixture was diluted with methanol and purified by preparative LCMS using pH 10 buffer to give the title compound as a racemic mixture (16 mg, 23%). LCMS calc. for C22H22N5O3 (M+H)+: m/z=404.2. found: 404.2. The isomers were separated by prep chiral column chromatography using the following conditions: Column: phenomenex Lux Cellulose C-2 5 μm, 21, 2×250 mm, Mobile phase: 45% EtOH/Hexanes, gradient condition: isocratic at 18 mL/min, Loading: 2.0 mg in 900 μL, run time: 24 min, peak time: 12.0, 14.0, 16.0 and 21.0 min.

Workup

  1. customThe title compound was prepared by methods analogous to Example 157
  2. customto 60 min
  3. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-33aabc9f9cbd4159b92df504b8356b8b
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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