Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1) → HCID 135481022, compound

HRID 2245580Notes

Reaction equation

HRID 2245580 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24]C)=O)[CH:20]=3)[NH:15][C:14]=2[OH:26])=[N:11][CH:12]=1)[CH2:4][CH3:5])[CH3:2].[ClH:27].[NH2:28][CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32]>C(#N)C>[ClH:27].[CH3:34][S:31]([CH2:30][CH2:29][NH:28][C:22]([C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([OH:26])=[C:13]2[C:10]1[CH:9]=[CH:8][C:7]([CH2:6][N:3]([CH2:1][CH3:2])[CH2:4][CH3:5])=[CH:12][N:11]=1)=[O:24])(=[O:33])=[O:32]

Participants

4

Reactant 2

HCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)HCID 136338403HCID 136338403, compound

Product 1

HCID 135481022HCID 135481022, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared as described for Example 67 using methyl 3-{5-[(diethylamino)methyl]pyridin-2-yl}-2-hydroxy-1H-indole-5-carboxylate (0.071 g, 0.2 mmol) and (2-aminoethyl)methylsulfone hydrochloride (0.080 g, 0.5 mmol) as starting materials. The base was obtained after preparative HPLC purification (XTerra®PrepMS C8 columns 10 μm, 19×300 mm; 0.1 M NH4OAc buffer/acetonitrile, from 90:10 to 40:60, as eluent gradient) as an orange yellow solid (0.030 g, 34% yield), which was transformed to the yellow hydrochloride salt (0.023 g, 72% yield): 1H NMR (CD3OD, 400 MHz) δ 8.21 (s, 1H), 8.11 (s, 1H), 7.95 (s, 2H), 7.60 (dd, J=8.0, 1.2 Hz, 1H), 7.14 (d, J=8.0 Hz, 1H), 4.35 (s, 2H), 3.93 (t, J=6.4 Hz, 2H), 3.51 (t, J=6.4 Hz, 2H), 3.29 (m, 4H), 3.09 (s, 3H), 1.43 (t, J=7.2 Hz, 6H); MS (EI) m/z 445 (M++1).

Workup

  1. customThe base was obtained

Sources & evidence

ORD record
ord-db29756a15d848b798691779441c508c
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

Loading…