Benzaldehyde → HCID 20627680, compound

HRID 23295Notes

Reaction equation

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

Participants

Reactant 2

HCID 240Benzaldehyde

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

Product 1

HCID 20627680HCID 20627680, compound

Procedure

Using 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 171. 1H NMR (CDCl3) δ: 7.42-7.25 (m, 5H), 6.37 (d, 1H, J=1.8 Hz), 6.26 (d, 1H, J=2.2 Hz), 4.27 (s, 2H), 3.69 (ABq, 2H, JAB=15.2 Hz), 3.60-3.50 (m, 1H), 3.37-3.30 (m, 1H), 3.28-3.20 (m, 1H), 3.10-2.85 (m, 6H), 2.62 (dd, 1H, J=12.8, 9.1 Hz), 1.89-1.80 (m, 2H). LRMS (ES)+: 352.4 (M+H)+.

Sources & evidence

ORD record: ord-f46edabb5ece464486bf4d15b764d0c5
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849619B2

Reaction notes

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