HCID 58691367, compound → Carbon Dioxide

HRID 1594476Notes

Reaction equation

HRID 1594476 reaction equation
[NH2:1][C:2]1[CH:11]=CC2[C:4](=[C:5]([O:12]C3N=CN=C(C4C=CC(C(F)(F)F)=CC=4N[C:30]([C@@H]4CCCCN4CC(C)C)=[O:31])C=3)C=CC=2)N=1.[NH2:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[C:46]([O:53][C:54]3[N:59]=[CH:58][N:57]=[C:56]([C:60]4[CH:65]=[CH:64][C:63]([C:66]([F:69])([F:68])[F:67])=[CH:62][C:61]=4[NH:70][C:71]([C@H:73]4[CH2:78][CH2:77][CH2:76][CH2:75][N:74]4[CH2:79][CH:80]([CH3:82])[CH3:81])=[O:72])[CH:55]=3)[CH:47]=[CH:48][CH:49]=2)[N:44]=1>>[C:30](=[O:31])=[O:53].[CH2:5]([OH:12])[CH3:4].[C:2](#[N:1])[CH3:11].[CH2:43]([NH:44][CH2:45][CH3:46])[CH3:52].[NH2:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[C:46]([O:53][C:54]3[N:59]=[CH:58][N:57]=[C:56]([C:60]4[CH:65]=[CH:64][C:63]([C:66]([F:69])([F:67])[F:68])=[CH:62][C:61]=4[NH:70][C:71]([CH:73]4[CH2:78][CH2:77][CH2:76][CH2:75][N:74]4[CH2:79][CH:80]([CH3:82])[CH3:81])=[O:72])[CH:55]=3)[CH:47]=[CH:48][CH:49]=2)[N:44]=1

Participants

5

Reactant 2

HCID 58691367HCID 58691367, compoundHCID 58691435HCID 58691435, compound

Product 3

HCID 280Carbon DioxideHCID 58691388HCID 58691388, compoundHCID 86607085HCID 86607085, compound

Procedure

(2S)-N-(2-(6-(2-Aminoquinolin-8-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)-phenyl)-1-isobutylpiperidine-2-carboxamide and (2R)-N-(2-(6-(2-Aminoquinolin-8-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenyl)-1-isobutylpiperidine-2-carboxamide. Chiral separation (Chiralpak ADH (250×21 mm, 5μ), A: liquid CO2, B: ethanol:acetonitrile:diethylamine (50:50:0.2), isocratic: 60:40 A:B, 60 mL/min, 24 mg/injection) of N-(2-(6-(2-aminoquinolin-8-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenyl)-1-isobutylpiperidine-2-carboxamide (Example 39) afforded the title compounds. MS (ESI, pos. ion.) m/z: 565 (M+1).

Workup

  1. customChiral separation (Chiralpak ADH (250×21 mm, 5μ)

Sources & evidence

ORD record
ord-ba0a43c00cac44e0a7930997b9226ca4
Source dataset
uspto-grants-2007_11
Patent number
US07301022B2

Reaction notes

Loading…