6-Chloro-5-methoxypyridin-3-amine → (S)-4-(2-(6-Chloro-5-methoxypyridin-3-ylamino)-5-((2-methyl-4-(methylsulfonyl)piperazin-1-YL)methyl)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1621916Notes

Reaction equation

HRID 1621916 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:9][CH3:10].F[C:12]1[C:17]([C:18]2[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([N:25](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:19]=2)=[CH:16][C:15]([CH2:44][N:45]2[CH2:50][CH2:49][N:48]([S:51]([CH3:54])(=[O:53])=[O:52])[CH2:47][C@@H:46]2[CH3:55])=[CH:14][N:13]=1>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:12]2[C:17]([C:18]3[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH2:25])[N:19]=3)=[CH:16][C:15]([CH2:44][N:45]3[CH2:50][CH2:49][N:48]([S:51]([CH3:54])(=[O:52])=[O:53])[CH2:47][C@@H:46]3[CH3:55])=[CH:14][N:13]=2)=[CH:4][C:3]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 234561436-Chloro-5-methoxypyridin-3-amineHCID 66611277(S)-4-(2-fluoro-5-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 59548337(S)-4-(2-(6-Chloro-5-methoxypyridin-3-ylamino)-5-((2-methyl-4-(methylsulfonyl)piperazin-1-YL)methyl)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Procedure

The title compound was prepared from 6-chloro-5-methoxypyridin-3-amine (Small Molecules, Inc.) and (S)-4-(2-fluoro-5-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (preparation similar as reported in Example 316, Steps 1 to 2; from (S)-tert-butyl 3-methylpiperazine-1-carboxylate (Sigma Aldrich, Inc.)) via similar steps as previously described in Example 316 and isolated as a yellow solid. m/z (ESI, +ve ion) 534 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.99-12.52 (m, 1H) 8.76-9.96 (m, 1H) 8.15-8.63 (m, 3H) 6.57-8.07 (m, 2H) 4.09-5.06 (m, 2H) 3.94 (s, 3H) 3.59-3.86 (m, 2H) 2.86-3.35 (m, 7H) 2.46 (s, 3H) 0.96-1.58 (m, 4H).

Workup

  1. customisolated as a yellow solid

Sources & evidence

ORD record
ord-8708a9ef528c43dbadd84308807a0014
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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