HCID 11242947, compound → HCID 11291280, compound

HRID 2377758Notes

Reaction equation

HRID 2377758 reaction equation
Cl[C:2]1[N:3]([CH2:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[C:4](=[O:9])[C:5]([Cl:8])=[CH:6][N:7]=1.[CH3:19][C@@:20]1([NH2:26])[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1>>[NH2:26][C@:20]1([CH3:19])[CH2:25][CH2:24][CH2:23][N:22]([C:2]2[N:3]([CH2:10][C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])[C:4](=[O:9])[C:5]([Cl:8])=[CH:6][N:7]=2)[CH2:21]1

Participants

3

Reactant 2

HCID 11242947HCID 11242947, compoundHCID 57518307HCID 57518307, compound

Product 1

HCID 11291280HCID 11291280, compoundYield 65%

Procedure

The title compound was prepared in 65% yield from 2-(2,5-dichloro-6-oxo-6H-pyrimidin-1-ylmethyl)-benzonitrile (Example 15B) and (R)-3-methyl-piperidin-3-ylamine according to the general procedure outlined for Example 1 and was isolated as the HCl salt. 1H NMR (400 MHz, DMSO-d6): δ 8.43 (br s, 3H), 8.09 (s, 1H), 7.80 (d, 1H, J=7.6 Hz), 7.64 (t, 1H, J=7.6 Hz), 7.45 (t, 1H, J=7.6 Hz), 7.22 (d, 1H, J=7.6 Hz), 5.39 (AB q, 2H, J=98.0, 14.8 Hz), 3.39-3.47 (m, 1H), 3.01-3.15 (m, 2H), 2.80-2.90 (m, 1H), 1.81-2.00 (m, 2H), 1.56-1.66 (m, 2H), 1.30 (m, 3H). MS (ES) [m+H] calc'd for C18H20N5OCl, 358, 360; found 358, 360.

Workup

  1. customwas isolated as the HCl salt

Sources & evidence

ORD record
ord-75088f9624404c3aaaa2beda029ab2da
Source dataset
uspto-grants-2008_12
Patent number
US07470700B2

Reaction notes

Loading…