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

HRID 1018849Notes

Reaction equation

HRID 1018849 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([CH2:35][CH:36]([N:40]2[CH2:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41]2=[O:49])[C:37](O)=[O:38])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:50][C:51]1[S:52][CH:53]=[CH:54][N:55]=1.C1(C[C@H](N2CC3C(=CC=CC=3)C2=O)C(NC2SC=CN=2)=O)CCCCC1>>[CH:28]1([CH2:35][CH:36]([N:40]2[CH2:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41]2=[O:49])[C:37]([NH:50][C:51]2[S:52][CH:53]=[CH:54][N:55]=2)=[O:38])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]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 184021683-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid

Product 1

HCID 102713163-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamideYield 97.6%

Procedure

BOP coupling of 3-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Step E; 173 mg; 0.58 mmol) and 2-aminothiazole (97 mg; 0.94 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) provided after flash chromatography (Biotage 40S, eluent: 35% ethyl acetate/hexanes) 217 mg (99%) of 3-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide as a white foam EI-HRMS m/e calcd for C21H25N3O2S (M+) 383.1667, found 383.1660.

Sources & evidence

ORD record
ord-fa289b5f15f14ddbab5ef53faf5ed938
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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