1-Bromo-2,3-dichlorobenzene → (7bR,11aS)-N-(2,3-dichlorophenyl)-1,2,7b,8,9,10,11,11 a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine

HRID 23265

반응식

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[Cl:9].[NH2:10][C:11]1[CH:12]=[C:13]2[C:17]3=[C:18]([CH2:20][S:21][CH2:22][CH2:23][N:16]3[C@H:15]3[CH2:24][CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27][C@@H:14]23)[CH:19]=1>>[Cl:9][C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[NH:10][C:11]1[CH:12]=[C:13]2[C:17]3=[C:18]([CH2:20][S:21][CH2:22][CH2:23][N:16]3[C@H:15]3[CH2:24][CH2:25][NH:26][CH2:27][C@@H:14]23)[CH:19]=1

참가 물질

반응물 2

HCID 420661-Bromo-2,3-dichlorobenzene

HCID 86586437tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H) carboxylate

생성물 1

HCID 60071808(7bR,11aS)-N-(2,3-dichlorophenyl)-1,2,7b,8,9,10,11,11 a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine

실험 절차

Using 1-bromo-2,3-dichlorobenzene and following the procedures described in EXAMPLE 33, Parts C and D, tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)Carboxylate from EXAMPLE 33, Part B was converted into the title compound of EXAMPLE 37 as a powder. 1H NMR (CDCl3,300 MHz) δ 1.79-1.89 (m, 2H), 2.58-2.69 (m, 1H), 2.79-3.25 (m, 7H), 3.41-3.50 (m, 1H), 3.60-3.68 (m, 2H), 3.74 (s, 2H), 6.01 (s, 1H), 6.73 (d, 1H, J=2 Hz), 6.81-6.85 (m, 3H), 6.95-6.98 (m 1H). LRMS (ES)+: 406 (M+H)+.

출처 및 근거

ORD 기록: ord-22d98f363aa94914b31e4939e9d8c9e8
출처 데이터셋: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06849619B2

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