Diisopropylethylamine → (4-Methanesulfonyl-piperazin-1-yl)-{5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-pyridin-3-yl}-methanone

HRID 2065575Notes

Reaction equation

HRID 2065575 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]([NH:15][C:16]3[CH:17]=[N:18][C:19]([CH3:25])=[C:20]([CH:24]=3)[C:21](O)=[O:22])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:59][S:60]([N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1)(=[O:62])=[O:61]>CN(C=O)C>[CH3:59][S:60]([N:63]1[CH2:68][CH2:67][N:66]([C:21]([C:20]2[C:19]([CH3:25])=[N:18][CH:17]=[C:16]([NH:15][C:12]3[N:13]=[CH:14][C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[CH:10][N:11]=3)[CH:24]=2)=[O:22])[CH2:65][CH2:64]1)(=[O:62])=[O:61]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7091611-(Methylsulfonyl)piperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581718975-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-nicotinic acid

Product 1

HCID 25211540(4-Methanesulfonyl-piperazin-1-yl)-{5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-pyridin-3-yl}-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-nicotinic acid 10 (0.05 mmol) in DMF (1 mL) is added HATU (0.06 mmol) and DIEA (0.14 mmol) at rt. The resulting mixture is stirred for 2 min then 1-methanesulfonyl-piperazine (0.05 mmol) is added. The reaction mixture is stirred at rt for 4 h and then directly purified by preparative LCMS to give (4-methanesulfonyl-piperazin-1-yl)-{5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-pyridin-3-yl}-methanone B1. 1H NMR (400 MHz, d4-CH3OH) δ 9.30 (d, J=4.0 Hz, 1H), 8.81 (s, 2H), 8.50 (d, J=4.0 Hz, 1H), 7.60-7.758 (m, 2H), 7.07-7.05 (m, 2H), 3.96-3.94 (m, 2H), 3.85 (s, 3H), 3.54-352 (m, 2H), 3.42-3.39 (m, 2H), 3.27 (bs, 2H), 2.91 (s, 3H), 2.62 (s, 3H). MS (m/z) (M+1)+: 483.1.

Workup

  1. stirringThe reaction mixture is stirred at rt for 4 h
  2. customdirectly purified by preparative LCMS

Sources & evidence

ORD record
ord-fb2aaec037d943a28c26428a923d15ff
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

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