2-Aminothiazole → 3-Cyclooctyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide

HRID 1018854Notes

Reaction equation

HRID 1018854 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([CH2:36][CH:37]([N:41]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]2=[O:50])[C:38]([OH:40])=O)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:51][C:52]1[S:53][CH:54]=[CH:55][N:56]=1.C1(C[C@H](N2CC3C(=CC=CC=3)C2=O)C(NC2SC=CN=2)=O)CCCCC1>>[CH:28]1([CH2:36][CH:37]([N:41]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]2=[O:50])[C:38]([NH:51][C:52]2[S:53][CH:54]=[CH:55][N:56]=2)=[O:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]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 184021673-Cyclooctyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid

Product 1

HCID 102721513-Cyclooctyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamideYield 87.5%

Procedure

BOP coupling of 3-Cyclooctyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Step D; 200 mg; 0.65 mmol) and 2-aminothiazole (70 mg; 0.70 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 flash chromatography (eluent: 30% ethyl acetate/hexanes) 226 mg (88%) of 3-Cyclooctyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide as a white foam: EI-HRMS m/e calcd for C22H27N3O2S (M+) 397.1824, found 397.1825.

Sources & evidence

ORD record
ord-4d0ce567f06d4ee3b0c41ab72847711a
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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