2-Aminothiazole → (S)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-pyrazin-2-yl-propionamide

HRID 1018842Notes

Reaction equation

HRID 1018842 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2C=CC=CC=2N=N1.C1(CC(N2CC3C(=CC=CC=3)C2=O)C(O)=O)CCCC1.NC1SC=CN=1.[CH:54]1([CH2:60][C@@H:61]([N:70]2[CH2:78][C:77]3[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=3)[C:71]2=[O:79])[C:62]([NH:64][C:65]2S[CH:67]=[CH:68][N:69]=2)=[O:63])[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1>>[CH:54]1([CH2:60][C@H:61]([N:70]2[CH2:78][C:77]3[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=3)[C:71]2=[O:79])[C:62]([NH:64][C:65]2[CH:12]=[N:8][CH:67]=[CH:68][N:69]=2)=[O:63])[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1

Participants

5

Reactant 4

HCID 21552-AminothiazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10133709(R)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamideHCID 184022093-Cyclopentyl-2-(1-oxoisoindolin-2-yl)propanoic acid

Product 1

HCID 10109378(S)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-pyrazin-2-yl-propionamide

Procedure

BOP coupling of (3-Cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Step A; 273 mg; 1.00 mmol) and 2-aminothiazole (100 mg; 1.00 mmol) in a manner similar to that used for the preparation of (R)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide (outlined in Example 9, Step B) provided after flash chromatography (Merck Silica gel 60, 230-400 mesh, eluent: 40% ethyl acetate/hexanes) 132 mg (37%) of 3-Cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide as a white solid: ES-HRMS m/e calcd for C19H21N3O2SNa (M++Na+) 378.1247, found 378.1250.

Sources & evidence

ORD record
ord-57d84659329043d5bd67e12568d2782d
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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