2-Chloro-5-(trifluoromethyl)benzaldehyde → (7bR,11aS)-N-[2-chloro-5-(trifluoromethyl)benzyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine

HRID 47574Notes

Reaction equation

HRID 47574 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=O.[NH2:14][C:15]1[CH:16]=[C:17]2[C:21]3=[C:22]([CH2:24][S:25][CH2:26][CH2:27][N:20]3[C@H:19]3[CH2:28][CH2:29][N:30](C(OC(C)(C)C)=O)[CH2:31][C@@H:18]23)[CH:23]=1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH2:4][NH:14][C:15]1[CH:16]=[C:17]2[C:21]3=[C:22]([CH2:24][S:25][CH2:26][CH2:27][N:20]3[C@H:19]3[CH2:28][CH2:29][NH:30][CH2:31][C@@H:18]23)[CH:23]=1

Participants

3

Reactant 2

HCID 6881812-Chloro-5-(trifluoromethyl)benzaldehydeHCID 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

Product 1

HCID 59984904(7bR,11aS)-N-[2-chloro-5-(trifluoromethyl)benzyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine

Procedure

Using 2-chloro-5-(trifluoromethyl)benzaldehyde and following the procedures described in EXAMPLE 126, 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 153. 1H NMR(CDCl3) δ: 9.20-9.05 (broad m, 2H), 7.67 (s, 1H), 7.52-7.40 (m, 2H), 6.43 (broad s, 1H), 6.32 (broad s, 1H), 4.39 (broad s, 2H), 4.35-4.10 (m, 2H), 3.75-3.30 (overlapping m, 4H), 3.30-2.79 (overlapping m, 5H), 2.65-2.50 (m, 1H), 2.20-2.05 (m, 2H). LRMS (ES)+: 454.4 (M+H)+.

Sources & evidence

ORD record
ord-6d10b81d36c544cabe8ed25ba9ea233a
Source dataset
uspto-grants-2004_03
Patent number
US06699852B2

Reaction notes

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