4-chloro-N-(2-(dimethylamino)ethyl)picolinamide → 4-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)-N-(2-(dimethylamino)ethyl)picolinamide

HRID 1809618Notes

Reaction equation

HRID 1809618 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[N:11]=[C:12]([NH:15][C:16]3[N:21]=[CH:20][C:19]([S:22][CH2:23][CH2:24][C:25](OC)=O)=[CH:18][C:17]=3[O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[S:13][CH:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].ClC1C=C[N:40]=[C:39]([C:43]([NH:45][CH2:46][CH2:47][N:48]([CH3:50])[CH3:49])=[O:44])[CH:38]=1>>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]2[N:11]=[C:12]([NH:15][C:16]3[N:21]=[CH:20][C:19]([S:22][C:23]4[CH:24]=[CH:25][N:40]=[C:39]([C:43]([NH:45][CH2:46][CH2:47][N:48]([CH3:49])[CH3:50])=[O:44])[CH:38]=4)=[CH:18][C:17]=3[O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[S:13][CH:14]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 430882584-chloro-N-(2-(dimethylamino)ethyl)picolinamideHCID 86631532Methyl 3-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate

Product 1

HCID 592916144-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)-N-(2-(dimethylamino)ethyl)picolinamide

Procedure

Prepared from methyl 3-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate and 4-chloro-N-(2-(dimethylamino)ethyl)picolinamide as described in Example 3, Step C. 1H NMR (CDCl3) δ 1.62-1.70 (m, 2H), 2.07-2.12 (m, 2H), 2.11 (s, 3H), 2.28 (s, 6H), 2.51 (t, 2H), 2.71 (t, 1H), 2.88 (tt, 1H), 3.19 (t, 1H), 3.52 (dd, 2H), 3.90 (d, 1H), 4.71 (d, 1H), 6.51 (s, 1H), 7.00 (dd, 1H), 7.09-7.15 (m, 3H), 7.21 (t, 1H), 7.40 (t, 2H), 7.80 (d, 1H), 8.22 (bs, 1H), 8.24 (d, 1H), 8.28 (d, 1H), 8.84 (bs, 1H).

Sources & evidence

ORD record
ord-eac4bf25ff224154929929ebab9d0936
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

Loading…