1-Methylpiperazine → Diethyl (4-{[4-{[2-methyl-7-(4-methylpiperazin-1-yl)-3-oxo-2,3-dihydro-1H-isoindol-4-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 1948003Notes

Reaction equation

HRID 1948003 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:32]=[CH:31][C:30]([N:33]4[CH2:38][CH2:37][N:36]([C:39](=O)C)[CH2:35][CH2:34]4)=[C:29]4[C:25]=3[C:26](=[O:43])[N:27]([CH3:42])[CH2:28]4)[C:20]([C:44]([F:47])([F:46])[F:45])=[CH:19][N:18]=2)=[CH:12][CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C(OP(CC1C=CC(NC2N=C(NC3C=CC(Br)=C4C=3C(=O)N(C)C4)C(C(F)(F)F)=CN=2)=CC=1)(=O)OCC)C.CN1CCNCC1>>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:32]=[CH:31][C:30]([N:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]4)=[C:29]4[C:25]=3[C:26](=[O:43])[N:27]([CH3:42])[CH2:28]4)[C:20]([C:44]([F:45])([F:47])[F:46])=[CH:19][N:18]=2)=[CH:12][CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 3

HCID 531671-MethylpiperazineHCID 58292897Diethyl [4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonateHCID 58293044Diethyl (4-{[4-{[7-(4-acetyl piperazin-1-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Product 1

HCID 58292886Diethyl (4-{[4-{[2-methyl-7-(4-methylpiperazin-1-yl)-3-oxo-2,3-dihydro-1H-isoindol-4-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Procedure

The title compound was prepared according to the procedure for Diethyl(4-{[4-{[7-(4-acetylpiperazin-1-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (Example 199) using Diethyl[4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate and the commerically available N-methylpiperazine. MS (ES+): m/z 648.35 (100) [MH+]; HPLC: tR=0.70 min (UPLC, purity).

Sources & evidence

ORD record
ord-7adb1867ca244e0d82e4634fea9d26f4
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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