Dichloromethane → (7bR,11aS)-N-[2-Ethoxy-3-pyridinyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-6-amine, bis hydrochloride salt

HRID 23298

반응식

HRID 23298 반응식
Br[C:2]1[C:3]([O:8][CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+].[NH2:17][C:18]1[CH:19]=[C:20]2[C:24]3=[C:25]([CH2:27][S:28][CH2:29][CH2:30][N:23]3[C@H:22]3[CH2:31][CH2:32][N:33](C(OC(C)(C)C)=O)[CH2:34][C@@H:21]23)[CH:26]=1.[Cl:42]CCl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Pd]>[ClH:42].[ClH:42].[CH2:9]([O:8][C:3]1[C:2]([NH:17][C:18]2[CH:19]=[C:20]3[C:24]4=[C:25]([CH2:27][S:28][CH2:29][CH2:30][N:23]4[C@H:22]4[CH2:31][CH2:32][NH:33][CH2:34][C@@H:21]34)[CH:26]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:10]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 109873083-Bromo-2-ethoxypyridineHCID 23676156Sodium t-butoxideHCID 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 131724731(7bR,11aS)-N-[2-Ethoxy-3-pyridinyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-6-amine, bis hydrochloride salt

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

실험 절차

Following the procedures described in Example 175 and using 3-bromo-2-ethoxypyridine, sodium tert-butoxide as the base and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane, as the palladium source, 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 186 as a solid. ESI MS m/z 383.2 [C21H26N4OS+H]+.

출처 및 근거

ORD 기록
ord-6ab698a3457d407d84690cf4ec0f1a57
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849619B2

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