4-Aminotetrahydropyran hydrochloride → 10-bromo-N3-(tetrahydro-2H-pyran-4-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2,3-dicarboxamide

HRID 575315

반응식

HRID 575315 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([C:19](O)=[O:20])=[C:14]([C:16](=[O:18])[NH2:17])[N:15]=[C:7]3[C:6]=2[CH:22]=1.Cl.[O:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]3[CH2:10][CH:9]([CH2:12]3)[N:8]3[C:13]([C:19]([NH:30][CH:27]4[CH2:28][CH2:29][O:24][CH2:25][CH2:26]4)=[O:20])=[C:14]([C:16]([NH2:17])=[O:18])[N:15]=[C:7]3[C:6]=2[CH:22]=1

참가 물질

3

반응물 2

HCID 441186934-Aminotetrahydropyran hydrochlorideHCID 8669334810-bromo-2-carbamoyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-3-carboxylic acid

생성물 1

HCID 8669335110-bromo-N3-(tetrahydro-2H-pyran-4-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2,3-dicarboxamide

실험 절차

10-bromo-2-carbamoyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-3-carboxylic acid (0.1 g) was reacted with tetrahydro-2H-pyran-4-amine hydrochloride similarly to the conditions described in Example 2 to produce 10-bromo-N3-(tetrahydro-2H-pyran-4-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2,3-dicarboxamide. This intermediate was then reacted with (2R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol via General Procedure E to afford 5.7 mg (10%) of 10-[(3R)-3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-ynyl]-N3-tetrahydropyran-4-yl-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2,3-dicarboxamide. M+1=516.

출처 및 근거

ORD 기록
ord-d736df2ce7844a5e820643229521317c
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

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