Benzo(d)thiazol-2-amine → N-Benzothiazol-2-yl-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide

HRID 1018829Notes

Reaction equation

HRID 1018829 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.C1(C[C@H](N2CC3C(=CC=CC=3)C2=O)C(O)=O)CCCCC1.NC1SC2C=CC=CC=2N=1.[CH:59]1([CH2:65][C@H:66]([N:75]2[CH2:83][C:82]3[C:77](=[CH:78][CH:79]=[CH:80][CH:81]=3)[C:76]2=[O:84])[C:67]([NH:69][C:70]2[S:71]C=CN=2)=[O:68])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1>>[S:71]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:70]1[NH:69][C:67](=[O:68])[CH:66]([N:75]1[CH2:83][C:82]2[C:77](=[CH:78][CH:79]=[CH:80][CH:81]=2)[C:76]1=[O:84])[CH2:65][CH:59]1[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64]1

Participants

5

Reactant 4

HCID 8706Benzo(d)thiazol-2-amineHCID 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 18402197N-Benzothiazol-2-yl-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamideYield 44%

Procedure

This compound was prepared via BOP coupling of (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Example 1, Step A, 144 mg; 0.5 mmol) and 2-amino-benzothiazole (81 mg; 0.55 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 9, Step B) to provide crude N-Benzothiazol-2-yl-3-cyclohexyl-2-( 1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide. The crude product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, eluent: 35% ethyl acetate/hexanes) to give 185 mg (44%) of N-Benzothiazol-2-yl-3-cyclohexyl-2-( 1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide as a white solid: EI-HRMS m/e calcd for C24H25N3O2S (M+) 419.1667, found 419.1661.

Workup

  1. customto provide crude N-Benzothiazol-2-yl-3-cyclohexyl-2-( 1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide
  2. customThe crude product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, eluent: 35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-23d7a01f919a49948d0096ba0537b776
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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