2-Aminoquinoline → 3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-quinolin-2-yl-propionamide

HRID 1018832Notes

Reaction equation

HRID 1018832 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH:28]1([CH2:34][C@H:35]([N:39]2[CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]2=[O:48])[C:36]([OH:38])=O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:49][C:50]1[CH:59]=[CH:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[N:51]=1.C1(C[C@H](N2CC3C(=CC=CC=3)C2=O)C(NC2SC=CN=2)=O)CCCCC1>>[CH:28]1([CH2:34][CH:35]([N:39]2[CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]2=[O:48])[C:36]([NH:49][C:50]2[CH:59]=[CH:58][C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[N:51]=2)=[O:38])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 4

HCID 113792-AminoquinolineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1477119(S)-3-Cyclohexyl-2-(1-oxoisoindolin-2-yl)propanoic acidHCID 9947513(S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide

Product 1

HCID 184021913-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-quinolin-2-yl-propionamideYield 99%

Procedure

This compound was prepared via BOP coupling of (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Step A of Example 1; 288 mg; 1.0 mmol) and 2-aminoquinoline (180 mg; 1.2 mmol) in a manner similar to that used for the preparation of (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide as outlined in Example 1, Step B) to provide 3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-quinolin-2-yl-propionamide as a white solid in 99% yield: EI-HRMS m/e calcd for C26H27N3O2 (M+) 413.2103, found 413.2103.

Sources & evidence

ORD record
ord-c5e3ff668d394392980a0a1dbbdfc2f4
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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