Reserpine → HCID 86603539, compound

HRID 645659Notes

Reaction equation

HRID 645659 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N:10]=[C:11]=[S:12].[CH3:13][C:14]1[C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=[CH:16][N:15]=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]([NH:21][CH2:20][C:19]1[C:14]([CH3:13])=[N:15][CH:16]=[CH:17][CH:18]=1)=[S:12]

Participants

5

Reactant 3

HCID 5770ReserpineHCID 11434939(2-methylpyridin-3-yl)methanamineHCID 86082271HCID 86082271, compound

Product 1

HCID 86603539HCID 86603539, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The title compound was prepared from 2,3-dichloro-4-fluorophenylisothiocyanate and C-(2-methylpyridin-3-yl)methylamine using General Procedure 1. 1H NMR (DMSO-d6, 400 MHz) 2.47 (s, 3H), 4.69 (m, 2H), 7.21 (dd, 1H, J=4.9 Hz, J=7.6 Hz), 7.46 (t, 1H, J=8.9 Hz), 7.54-7.67 (bs, 1H), 7.58 (dd, 1H, J=1.4 Hz, J=7.7 Hz), 8.26-8.42 (bs, 1H), 8.33 (dd, 1H, J=1.7 Hz, J=4.8 Hz), 9.49 (s, 1H); RP-HPLC (Hypersil®-100 C18, 5 μm, 100 Å, 10 cm; 5%-100% acetonitrile-0.1M ammonium acetate over 5 min, 2 mL/min), then 100% acetonitrile isocratic 1 minutes, Rt 3.69 min. (90.8%); MS: M+H− 342.

Sources & evidence

ORD record
ord-9c6121c06ee94025b60547e1ee1eb3f3
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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