2-Aminopyridine → HCID 10177635, compound

HRID 1018870Notes

Reaction equation

HRID 1018870 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:11]=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][C:45]=3Cl)[C:40]2=[O:49])[C:36]([OH:38])=O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][N:52]=1.C1(C[C@H](N2CC3C(=CC=CC=3)C2=O)C(NC2SC=CN=2)=O)CCCCC1>>[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:49])[C:36]([NH:50][C:51]2[CH:56]=[CH:55][C:54]([CH3:11])=[CH:53][N:52]=2)=[O:38])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 4

HCID 104392-AminopyridineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 9947513(S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamideHCID 69694579HCID 69694579, compound

Product 1

HCID 10177635HCID 10177635, compoundYield 30%

Procedure

BOP coupling of (S)-3-cyclohexyl-2-(4-Chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (ca. 1:1 mixture of regioisomers, prepared in Example 36, Step C; 201 mg; 0.62 mmol) and 2-aminopyridine(132 mg; 1.39 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 9, Step B) provided after chromatography (Biotage 40S column, eluent: 30% ethyl acetate/hexanes) 107 mg of (S)-3-Cyclohexyl-2-(4-Chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-N-pyridin-2-yl-propionamide: EI-HRMS m/e calcd for C22H24ClN3O2 (M+) 397.1557, found 397.1563; and 46 mg of regioisomeric (S)-3-Cyclohexyl-2-(7-Chloro-1-oxo-1,3dihydro-isoindol-2-yl)-N-pyridin-2-yl-propionamide: EI-HRMS m/e calcd for C22H24ClN3O2 (M+) 397.1557, found 397.1551.

Sources & evidence

ORD record
ord-6bc738a198d84ddb86d88f1a9876d43e
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

Loading…