Triethylamine → (6-Amino-pyridin-3-yl)-{4-[6-(2-fluoro-4-methanesulfonyl-phenoxy)-5-methyl-pyrimidin-4-yloxy]-piperidin-1-yl}-methanone

HRID 1036792Notes

Reaction equation

HRID 1036792 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[F:42][C:43]1[CH:63]=[C:62]([S:64]([CH3:67])(=[O:66])=[O:65])[CH:61]=[CH:60][C:44]=1[O:45][C:46]1[C:51]([CH3:52])=[C:50]([O:53][CH:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[N:49]=[CH:48][N:47]=1>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:57]2[CH2:58][CH2:59][CH:54]([O:53][C:50]3[C:51]([CH3:52])=[C:46]([O:45][C:44]4[CH:60]=[CH:61][C:62]([S:64]([CH3:67])(=[O:65])=[O:66])=[CH:63][C:43]=4[F:42])[N:47]=[CH:48][N:49]=3)[CH2:55][CH2:56]2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672020214-(2-Fluoro-4-methanesulfonyl-phenoxy)-5-methyl-6-(piperidin-4-yloxy)-pyrimidine

Product 1

HCID 11752400(6-Amino-pyridin-3-yl)-{4-[6-(2-fluoro-4-methanesulfonyl-phenoxy)-5-methyl-pyrimidin-4-yloxy]-piperidin-1-yl}-methanoneYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Amino-nicotinic acid (21.5 mg, 0.155 mmol), HATU (59 mg, 0.155 mmol) and triethylamine (0.05 mL, 0.359 mmol) were mixed in DMF and stirred at rt for 20 min. 4-(2-Fluoro-4-methanesulfonyl-phenoxy)-5-methyl-6-(piperidin-4-yloxy)-pyrimidine was then added and the mixture stirred at rt for 2 h. The crude was purified by HPLC to afford Compound C5 as a yellow solid (67 mg, 90.7%). 1H NMR (CDCl3, 400 MHz) δ 1.88-1.87 (m, 2H), 1.99-2.01 (m, 2H), 2.15 (s, 3H), 3.03 (s, 3H), 3.58-3.60 (m, 2H), 3.77-3.78 (m, 2H), 5.37-5.41 (m, 1H), 6.78-6.82 (d, 1H), 7.33-7.38 (m, 1H), 7.69-7.74 (m, 2H), 7.87-7.96 (m, 2H), 8.14 (s, 1H). Exact mass calculated for C23H24FN5O5S 501.15, found 502.4 (MH+).

Workup

  1. stirringthe mixture stirred at rt for 2 h
  2. customThe crude was purified by HPLC

Sources & evidence

ORD record
ord-35c0acf70e1049c2ab4d4cd9fab8b65f
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

Loading…