2-Amino-5-chlorothiazole hydrochloride → N-(5-Chloro-thiazol-2-yl)-3-cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide

HRID 1018850Notes

Reaction equation

HRID 1018850 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]([OH:39])=O)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.Cl.[NH2:51][C:52]1[S:53][C:54]([Cl:57])=[CH:55][N:56]=1.C1(C[C@H](N2CC3C(=CC=CC=3)C2=O)C(NC2SC=CN=2)=O)CCCCC1>>[Cl:57][C:54]1[S:53][C:52]([NH:51][C:37](=[O:39])[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])[CH2:35][CH:28]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[N:56][CH:55]=1

Participants

5

Reactant 4

HCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 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 10273487N-(5-Chloro-thiazol-2-yl)-3-cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamideYield 40.1%

Procedure

BOP coupling of 3-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Step E; 177 mg; 0.59 mmol) and 2-amino-5-chlorothiazole hydrochloride (168 mg; 0.95 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 40M, eluent: 20% ethyl acetate/hexanes) 99 mg (40%) of N-(5-Chloro-thiazol-2-yl)-3-cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide as an off white foam EI-HRMS m/e calcd for C21H24ClN3O2S (M+) 417.1278, found 417.1289.

Sources & evidence

ORD record
ord-d2812026a1f041398ab19992e6ff7421
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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