2-Aminothiazole → HCID 18402181, compound

HRID 1018834Notes

Reaction equation

HRID 1018834 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]=[C:44]([N+:48]([O-:50])=[O:49])[CH:45]=3)[C:40]2=[O:51])[C:36](O)=[O:37])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:52][C:53]1[S:54][CH:55]=[CH:56][N:57]=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]=[C:44]([N+:48]([O-:50])=[O:49])[CH:45]=3)[C:40]2=[O:51])[C:36]([NH:52][C:53]2[S:54][CH:55]=[CH:56][N:57]=2)=[O:37])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 4

HCID 21552-AminothiazoleHCID 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 69696537HCID 69696537, compound

Product 1

HCID 18402181HCID 18402181, compoundYield 34.7%

Procedure

BOP coupling of (S)-3-cyclohexyl-2-(5-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (ca. 1:1 mixture of regioisomers, prepared in Step C; 301 mg; 0.91 mmol) and 2-aminothiazole (116 mg; 1.12 mol) 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) provided after chromatography (Biotage 40M, eluent: 30% ethyl acetate/hexanes) 131 mg of 3-Cyclohexyl-2-(5-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide: EI-HRMS m/e calcd for C20H22N4O4S (M+) 414.1362, found 414.1362 and 121 mg of regioisomeric 3-Cyclohexyl-2-(6-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide: EI-HRMS m/e calcd for C20H22N4O4S (M+) 414.1362, found 414.1368.

Sources & evidence

ORD record
ord-f94321ad988248608f8acbc8c738d816
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

Loading…