3-Methyl-3H-imidazo[4,5-b]pyridin-6-amine → HCID 59548248, compound

HRID 1621704Notes

Reaction equation

HRID 1621704 reaction equation
F[C:2]1[C:7]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:9]=2)=[CH:6][C:5]([CH2:34][N:35]2[CH2:40][CH2:39][N:38]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:37][CH2:36]2)=[CH:4][N:3]=1.[CH3:45][N:46]1[C:50]2=[N:51][CH:52]=[C:53]([NH2:55])[CH:54]=[C:49]2[N:48]=[CH:47]1>>[NH2:15][C:10]1[N:11]=[C:12]([CH3:14])[N:13]=[C:8]([C:7]2[C:2]([NH:55][C:53]3[CH:54]=[C:49]4[N:48]=[CH:47][N:46]([CH3:45])[C:50]4=[N:51][CH:52]=3)=[N:3][CH:4]=[C:5]([CH2:34][N:35]3[CH2:40][CH2:39][N:38]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:37][CH2:36]3)[CH:6]=2)[N:9]=1

Participants

3

Reactant 2

HCID 232983793-Methyl-3H-imidazo[4,5-b]pyridin-6-amineHCID 666116314-(2-fluoro-5-((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 59548248HCID 59548248, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 197 (starting from Step 2) using 4-(2-fluoro-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (388 mg, 0.624 mmol) and 3-methyl-3H-imidazo[4,5-b]pyridin-6-amine (Adesis) as starting materials. 1H NMR (400 MHz, d6-DMSO) δ 12.00 (s, 1H); 8.73 (d, J=2.3 Hz, 1H); 8.67 (m, 2H); 8.36 (s, 1H); 8.26 (d, J=2.5 Hz, 1H); 7.93 (br, 1H); 7.74 (br, 1H); 3.84 (s, 3H); 3.50 (s, 2H); 3.11 (m, 4H); 2.87 (s, 3H); 2.48-2.49 (m, 4H); 2.49 (m, 3H). m/z (ESI, +ve ion) 510 (M+H)+.

Sources & evidence

ORD record
ord-971b9029409d4e6aac76d42aab610185
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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