Diisopropylethylamine → 4-{5-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]pyridine-2-carbonyl}-piperazin-2-one
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]=[CH:18][C:19]([C:22](O)=[O:23])=[N:20][CH:21]=3)=[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.[NH:58]1[CH2:63][CH2:62][NH:61][CH2:60][C:59]1=[O:64]>CN(C=O)C>[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]=[CH:18][C:19]([C:22]([N:61]4[CH2:62][CH2:63][NH:58][C:59](=[O:64])[CH2:60]4)=[O:23])=[N:20][CH:21]=3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid 5 (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 and then piperazine-2-one (0.05 mmol) is added. The reaction mixture is stirred at it for 12 h and then directly purified by preparative LCMS to give 4-{5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]pyridine-2-carbonyl}-piperazin-2-one A2 as a white solid. 1H NMR (400 MHz, d4-CH3OH) δ 8.98 (d, J=4.0 Hz, 1H), 8.77 (s, 1H), 8.53-8.52 (m, 2H), 7.74-7.73 (m, 2H), 7.58-7.56 (m, 2H), 7.07-7.05 (m, 2H), 3.94 (bs, 2H), 3.81 (s, 3H), 3.46 (bs, 2H), 3.45 (bs, 2H). MS (m/z) (M+1)+: 405.2.
Workup
- stirringThe reaction mixture is stirred at it for 12 h
- customdirectly purified by preparative LCMS
Sources & evidence
- ORD record
- ord-49153ed23c3f479cbf5874b71f84634e
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288540B2
Reaction notes
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