HCID 59452860, compound → HCID 59452583, compound

HRID 419538Notes

Reaction equation

[CH3:1][S:2]([CH2:5][CH2:6][N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([CH2:22][CH2:23][CH3:24])[CH:14]=2)[CH2:9][CH2:8]1)(=[O:4])=[O:3].C1[C@@H]2CN(C3CCN(C4C=CC(N)=C(OC)C=4)CC3)CCN2CCO1>>[CH3:1][S:2]([CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([CH2:22][CH2:23][CH3:24])[CH:14]=2)[CH2:11][CH2:12]1)(=[O:4])=[O:3]

Participants

Reactant 2

HCID 59452860HCID 59452860, compound

HCID 59452872HCID 59452872, compound

Product 1

HCID 59452583HCID 59452583, compoundYield 74%

Procedure

The title compound of step D (0.249 g, 0.770 mmol, 74%) was prepared from 1-[2-(methylsulfonyl)ethyl]-4-(4-nitro-3-propylphenyl)-1,2,3,6-tetrahydropyridine in an analogous manner to that of 4-{4-[(9aS)-hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-1-piperidinyl}-2-(methyloxy)aniline (Example 87, step I). 1H NMR (400 MHz, CDCl3) δ ppm 1.00 (t, J=7.3 Hz, 3H), 1.61-1.71 (m, 4H), 1.83 (d, J=14.3 Hz, 2H), 2.14 (td, J=11.7, 2.2 Hz, 2H), 2.38 (dt, J=12.0, 3.7 Hz, 1H), 2.41-2.47 (m, 2H), 2.89 (t, J=6.4 Hz, 2H), 3.01 (d, J=11.4 Hz, 2H), 3.06 (s, 3H), 3.17 (t, J=6.4 Hz, 2H), 3.54 (br. s., 2H), 6.60-6.64 (m, 1H), 6.85-6.89 (m, 2H).

Sources & evidence

ORD record: ord-e42dddb12a5e4bff8b5931e503c86a0f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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