Reserpine → HCID 68679245, compound

HRID 645666

Reaction equation

HRID 645666 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H:23]2[C@@H:14]([CH2:15][N:16]3[C@H:21]([CH2:22]2)C2NC4C=C(OC)C=CC=4C=2CC3)[CH2:13][C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O.C(#[N:55])C>>[F:1][C:2]1[C:7]([O:8][C:15]2[N:16]=[CH:21][CH:22]=[CH:23][C:14]=2[C:13]#[N:55])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 5770ReserpineHCID 6342Acetonitrile2×HCID 27627852-Fluoro-3-hydroxypyridine

Product 1

HCID 68679245HCID 68679245, compound

Procedure

The title compound was synthesized by General Procedure 9 using 2-fluoro-3-hydroxypyridine. 1H NMR (DMSO-d6. 400 MHz) δ 7.41 (dd, 1H, J=5.0 Hz, J=7.6 Hz), 7.51 (ddd, 1H, J=1.1 Hz, J=4.9 Hz, J=7.8 Hz), 8.09 (ddd, 1H, J=1.7 Hz, J=7.8 Hz, J=9.7 Hz), 8.19 (td, 1H, J=1.6 Hz, J=4.9 Hz), 8.42 (dd, 1H, J=1.9 Hz, J=5.0 Hz), 8.50 (dd, 1H, J=1.9 Hz, J=7.6 Hz); RP-HPLC (Hypersil®1-100 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 3.62 min.

Sources & evidence

ORD record
ord-03fa5e3ee3b7490c93c65bd7c6d03996
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Linked notes

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