Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → N-(5-Bromo-thiazol-2-yl)-3-cyclohexyl-2-(5,6-dichloro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide

HRID 1018827

반응식

HRID 1018827 반응식
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][C:43]([Cl:49])=[C:44]([Cl:48])[CH:45]=3)[C:40]2=[O:50])[C:36](O)=[O:37])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.Cl.[NH2:52][C:53]1[S:54][C:55]([Br:58])=[CH:56][N:57]=1.C1(C[C@H](N2CC3C(=CC=CC=3)C2=O)C(NC2SC=CN=2)=O)CCCCC1>>[Br:58][C:55]1[S:54][C:53]([NH:52][C:36](=[O:37])[CH:35]([N:39]2[CH2:47][C:46]3[C:41](=[CH:42][C:43]([Cl:49])=[C:44]([Cl:48])[CH:45]=3)[C:40]2=[O:50])[CH2:34][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)=[N:57][CH:56]=1

참가 물질

5

반응물 4

HCID 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 221703925-Bromo-1,3-thiazol-2-amine--hydrogen chloride (1/1)HCID 69695408HCID 69695408, 화합물

생성물 1

HCID 18402213N-(5-Bromo-thiazol-2-yl)-3-cyclohexyl-2-(5,6-dichloro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide수율 40%

실험 절차

This compound was prepared via BOP coupling of (S)-3-cyclohexyl-2-(5,6-dichloro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Example 4, Step C; 248 mg; 0.70 mmol) and 2-amino-5-bromothiazole hydrochloride (154 mg; 0.89 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) to provide N-(5-Bromo-thiazol-2-yl)-3-cyclohexyl-2-(5,6-dichloro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide as a beige solid in 40% yield: EI-HRMS m/e calcd for C20H20BrCl2N3O2S (M+) 514.9837, found 514.9836.

출처 및 근거

ORD 기록
ord-b3945481f3214f2f92e695b06dc289c2
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482951B2

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