2-Aminoimidazole → HCID 9903153, compound

HRID 1018857Notes

Reaction equation

HRID 1018857 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]=[CH:44][CH:45]=3)[C:40]2=[O:48])[C:36](O)=[O:37])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:49][C:50]1[NH:51][CH:52]=[CH:53][N:54]=1.C1(C[C@H](N2CC3C(=CC=CC=3)C2=O)C(NC2SC=CN=2)=O)CCCCC1>>[CH:28]1([CH2:34][C@H:35]([N:39]2[CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]2=[O:48])[C:36]([NH:49][C:50]2[NH:51][CH:52]=[CH:53][N:54]=2)=[O:37])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 4

HCID 821402-AminoimidazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1477119(S)-3-Cyclohexyl-2-(1-oxoisoindolin-2-yl)propanoic acidHCID 9947513(S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide

Product 1

HCID 9903153HCID 9903153, compoundYield 90.8%

Procedure

BOP coupling of (S)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Example 1, Step A; 287 mg; 1.00 mmol) and 2-aminoimidazole (241 mg; 1.79 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 (outlined in Example 1, Step B) provided after flash chromatography (Biotage 40M; eluent: 4% methanol/methylene chloride) 320 mg of (S)-3-Cyclohexyl-N-(1H-imidazol-2-yl)-2-(1-oxo-1,3-dihydro-isoindol-2-yl) propionamide which was then recrystallized from ethyl acetate/hexanes to give 209 mg of pure material: EI-HRMS m/e calcd for C20H24N4O2 (M+) 352.1899, found 352.1895.

Sources & evidence

ORD record
ord-ee8dab6d2c3a449b8371f72af6e189c2
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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