2,4-Difluorobenzaldehyde → (7bR,11aS)-N-(2,4-difluorobenzyl)-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 47581

Reaction equation

HRID 47581 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:11][C:12]1[CH:13]=[C:14]2[C:18]3=[C:19]([CH2:21][S:22][CH2:23][CH2:24][N:17]3[C@H:16]3[CH2:25][CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28][C@@H:15]23)[CH:20]=1>>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:11][C:12]1[CH:13]=[C:14]2[C:18]3=[C:19]([CH2:21][S:22][CH2:23][CH2:24][N:17]3[C@H:16]3[CH2:25][CH2:26][NH:27][CH2:28][C@@H:15]23)[CH:20]=1

Participants

3

Reactant 2

HCID 737702,4-DifluorobenzaldehydeHCID 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 20627674(7bR,11aS)-N-(2,4-difluorobenzyl)-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 2,4-difluorobenzaldehyde 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 P was converted into the title compound of EXAMPLE 163. 1H NMR(CDCl3) δ: 7.30-7.20 (m, 1H), 6.80-6.70 (m, 2H), 6.27 (d, 1H, J=2.2 Hz), 6.15 (d, 1H, J=2.2 Hz), 4.20 (broad s, 2H), 3.59 (ABq, 2H, JAB=15.2 Hz), 3.53-3.40 (m, 2H), 3.29-3.21 (m, 1H), 3.20-3.10 (m, 1H), 3.02-2.77 (m, 5H), 2.52 (dd, 1H, J=12.8, 9.2 Hz), 1.82-1.70 (m, 2H). LRMS (ES)+: 388.4 (M+H)+.

Sources & evidence

ORD record
ord-061f0ba685d743ea8247b7ddca23fa4f
Source dataset
uspto-grants-2004_03
Patent number
US06699852B2

Linked notes

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