Methane → (6bR,10aS)-5-(2,4-dichlorophenyl)-1,2,6b,7,8,9,10,10a-octahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole 3,3-dioxide hydrochloride

HRID 1764914Notes

Reaction equation

HRID 1764914 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:15]3=[C:16]([S:18](=[O:22])(=[O:21])[CH2:19][CH2:20][N:14]3[C@H:13]3[CH2:23][CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][C@@H:12]23)[CH:17]=1.C>>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:15]3=[C:16]([S:18](=[O:21])(=[O:22])[CH2:19][CH2:20][N:14]3[C@H:13]3[CH2:23][CH2:24][NH:25][CH2:26][C@@H:12]23)[CH:17]=1

Participants

3

Reactant 2

HCID 297MethaneHCID 21302653HCID 21302653, compound

Product 1

HCID 69514236(6bR,10aS)-5-(2,4-dichlorophenyl)-1,2,6b,7,8,9,10,10a-octahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole 3,3-dioxide hydrochlorideYield 162.6%

Procedure

The title compound (37 mg, 80%) was prepared from tert-butyl(6bR,10aS)-5-(2,4-dichlorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4hi]indole-8(7H)-carboxylate 3,3-dioxide (52 mg) using the procedure described in Example 448 Step B. 1H NMR (CD3OD, 500 MHz) δ2.20-2.25 (m, 1H), 2.25-2.35 (m, 1H), 3.00 (t, 1H, 12.5 Hz), 3.18-3.38 (m, 3H), 3.45-3.75 (m, 5H), 3.83-3.95 (m, 2H), 7.35 (d, 1H, J=6.8 Hz), 7.40 (m, 1H), 7.49 (m, 1H), 7.51 (m, 1H), 7.59 (m, 1H) ppm. CIMS (Methane) m/z=410 [C19H18Cl2N2O2S+H]+.

Sources & evidence

ORD record
ord-d4d60cc4ec5643449436d03c51a8a8a5
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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