1-(Methylsulfonyl)piperazine → HCID 59548309, compound

HRID 1812008Notes

Reaction equation

HRID 1812008 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:32]=[O:33])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=3)[N:10]=2)=CC=1.[CH3:45][S:46]([N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1)(=[O:48])=[O:47]>>[F:29][C:27]1[CH:28]=[C:23]([NH:22][C:21]2[C:16]([C:11]3[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([NH2:8])[N:10]=3)=[CH:17][C:18]([C:32]([N:52]3[CH2:53][CH2:54][N:49]([S:46]([CH3:45])(=[O:48])=[O:47])[CH2:50][CH2:51]3)=[O:33])=[CH:19][N:20]=2)[CH:24]=[N:25][C:26]=1[O:30][CH3:31]

Participants

3

Reactant 2

HCID 7091611-(Methylsulfonyl)piperazineHCID 715003625-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 59548309HCID 59548309, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 151 using 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinecarbaldehyde and 1-methanesulfonylpiperazine (Oakwood Products, West Columbia, S.C.), and the desired product 4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-((4-(methylsulfonyl)-1-piperazinyl)carbonyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine was isolated as a yellow solid (52% for two steps). 1H NMR (400 MHz, d6-DMSO) δ 12.11 (s, 1H) 8.85-8.93 (m, 1H) 8.45 (dd, J=2.15, 0.39 Hz, 1H) 8.42 (d, J=2.35 Hz, 1H) 8.30-8.39 (m, 1H) 7.95 (br. s., 1H) 7.83 (br. s., 1H) 3.95 (s, 3H) 3.61-3.73 (m, 4H) 3.19 (t, 4H) 2.91 (s, 3H) 2.45 (s, 3H). m/z (ESI, +ve ion) 518.0 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that

Sources & evidence

ORD record
ord-92e3117573ab4722854bce7652f345ba
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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