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

HRID 1621917Notes

Reaction equation

HRID 1621917 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.F[C:10]1[C:15]([C:16]2[N:21]=[C:20]([CH3:22])[N:19]=[C:18]([N:23](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:17]=2)=[CH:14][C:13]([CH2:42][N:43]2[CH2:48][CH2:47][N:46]([S:49]([CH3:52])(=[O:51])=[O:50])[CH2:45][C@@H:44]2[CH3:53])=[CH:12][N:11]=1>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:10]2[C:15]([C:16]3[N:21]=[C:20]([CH3:22])[N:19]=[C:18]([NH2:23])[N:17]=3)=[CH:14][C:13]([CH2:42][N:43]3[CH2:48][CH2:47][N:46]([S:49]([CH3:52])(=[O:50])=[O:51])[CH2:45][C@@H:44]3[CH3:53])=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 793055-Amino-2-chloropyridineHCID 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 59548212(S)-4-(2-(6-Chloropyridin-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-chloropyridin-3-amine (Sigma Aldrich, 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) 504 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 12.16 (s, 1H) 8.88 (d, J=2.74 Hz, 1H) 8.73 (d, J=2.35 Hz, 1H) 8.47 (dd, J=8.71, 2.84 Hz, 1H) 8.31 (d, J=2.35 Hz, 1H) 7.93 (br. s., 1H) 7.78 (br. s., 1H) 7.45 (d, J=8.61 Hz, 1H) 3.94 (d, J=13.11Hz, 1H) 3.07-3.29 (m, 3H) 2.86-2.97 (m, 1H) 2.85 (s, 3H) 2.64-2.79 (m, 2H) 2.54-2.64 (m, 1H) 2.45 (s, 3H) 2.14-2.29 (m, 1H) 1.16 (d, J=6.06 Hz, 3H).

Workup

  1. customisolated as a yellow solid

Sources & evidence

ORD record
ord-ae41e1c0893546ba8c3c5bac22c85f06
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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