2-Acetylthiazole → (R)-2,6-dimethyl-5-(6-(2-(2-methylpyrrolidin-1-yl)ethyl)quinolin-2-yl)nicotinamide

HRID 273239

Reaction equation

HRID 273239 reaction equation
C(C1C(C)=NC(C)=C(C=1)C#N)(=[O:3])C.S1C=CN=C1C(=O)C.[CH3:22][C:23]1[N:30]=[C:29]([CH3:31])[C:28]([C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[C:37]([CH2:42][CH2:43][N:44]4[CH2:48][CH2:47][CH2:46][C@H:45]4[CH3:49])[CH:38]=3)[N:33]=2)=[CH:27][C:24]=1[C:25]#[N:26]>>[CH3:22][C:23]1[N:30]=[C:29]([CH3:31])[C:28]([C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[C:37]([CH2:42][CH2:43][N:44]4[CH2:48][CH2:47][CH2:46][C@H:45]4[CH3:49])[CH:38]=3)[N:33]=2)=[CH:27][C:24]=1[C:25]([NH2:26])=[O:3]

Participants

4

Reactant 3

HCID 5201082-AcetylthiazoleHCID 27959485-Acetyl-2,6-dimethylnicotinonitrileHCID 46890475(R)-2,6-dimethyl-5-(6-(2-(2-methylpyrrolidin-1-yl)ethyl)quinolin-2-yl)nicotinonitrile

Product 1

HCID 25156752(R)-2,6-dimethyl-5-(6-(2-(2-methylpyrrolidin-1-yl)ethyl)quinolin-2-yl)nicotinamide

Procedure

The title compound was prepared using the procedure described in Example 57 using 5-acetyl-2,6-dimethylnicotinonitrile for 1-(1,3-thiazol-2-yl)ethanone providing the product from Example 67 which eluted first and the title compound which eluted second. 1H NMR (CDCl3) δ ppm 1.18 (d, J=5.43 Hz, 3 H), 1.53 (m, 1 H), 1.80 (m, 2 H), 1.98 (m, 1 H), 2.2-2.6 (m, 3 H), 2.65 (s, 3 H), 2.78 (s, 3 H), 3.09 (m, 2 H), 3.19 (m, 1 H), 3.33 (m, 1 H), 5.75 (s, 1 H), 5.90 (s, 1H), 7.52 (d, J=8.48 Hz, 1 H), 7.66 (dd, J=8.65, 1.87 Hz, 1 H), 7.71 (s, 1 H), 7.94 (s, 1 H), 8.06 (d, J=8.82 Hz, 1 H), 8.19 (d, J=8.14 Hz, 1 H). MS (DCl—NH3) [M+H]+ at 389.

Workup

  1. washeluted first
  2. washthe title compound which eluted second

Sources & evidence

ORD record
ord-758cde2e29564100b665d89a8d5d74de
Source dataset
uspto-grants-2008_11
Patent number
US07456196B2

Linked notes

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