Reserpine → HCID 86603540, compound

HRID 645660Notes

Reaction equation

HRID 645660 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].[N:13]1[C:22]2[CH2:21][CH2:20][CH2:19][CH:18]([NH2:23])[C:17]=2[CH:16]=[CH:15][CH:14]=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:23][CH:18]1[CH2:19][CH2:20][CH2:21][C:22]2[N:13]=[CH:14][CH:15]=[CH:16][C:17]1=2)=[S:12]

Participants

5

Reactant 3

HCID 5770ReserpineHCID 1561825,6,7,8-Tetrahydroquinolin-5-amineHCID 86082271HCID 86082271, compound

Product 1

HCID 86603540HCID 86603540, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The title compound was prepared from 2,3-dichloro-4-fluorophenylisothiocyanate and 5,6,7,8-tetrahydroquinolin-5-ylamine using General Procedure 1. 1H NMR (DMSO-d6, 400 MHz) 1.77-1.93 (m, 2H), 1.93-2.12 (m, 2H), 2.81-2.97 (m, 2H), 5.70-5.83 (m, 1H), 7.28 (dd, 1H, J=4.7 Hz, J=7.8 Hz), 7.51 (t, 1H, J=8.9 Hz), 7.62-7.78 (m, 2H), 8.37 (d, 1H, J=8.5 Hz), 8.43 (dd, 1H, J=1.4 Hz, J=4.5 Hz), 9.39 (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 min. (98.9%); MS: M+H+ 370.

Sources & evidence

ORD record
ord-7128a0ade5864afcb9c4b0a47beb999a
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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