(R)-3-Pyrrolidinol → HCID 90409770, compound

HRID 589140Notes

Reaction equation

HRID 589140 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.[CH2:27]1[C@@H:31]([OH:32])[CH2:30][NH:29][CH2:28]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:29]5[CH2:28][CH2:27][C@@H:31]([OH:32])[CH2:30]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 2759337(R)-3-PyrrolidinolHCID 90408846HCID 90408846, compound

Product 1

HCID 90409770HCID 90409770, 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 and 3R-pyrrolidinol. The mixture was diluted with methanol and purified by preparative LCMS using pH 10 buffer to afford the title compound as a mixture of diastereomers (13.3 mg, 75%). LCMS calc. for C23H24N5O3 (M+H)+: m/z=418.2. found: 418.2. 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: 5.0 mg in 900 μL, run time: 18 min, peak time: 12.0, 14.0 and 16.0 min.

Workup

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

Sources & evidence

ORD record
ord-9f894fc885c34128ac2228439e64f097
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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