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 511433Notes

Reaction equation

HRID 511433 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:21][C:22]3[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][N:25]=[C:24]([NH:32][C:33]4[CH:47]=[CH:46][C:36]([CH2:37][P:38](=[O:45])([O:42][CH2:43][CH3:44])[O:39][CH2:40][CH3:41])=[CH:35][CH:34]=4)[N:23]=3)=[C:14]3[C:18]=2[CH2:17][N:16]([CH3:19])[C:15]3=[O:20])[CH2:6][CH2:5]1)(=O)C.BrC1C=CC(NC2C(C(F)(F)F)=CN=C(NC3C=CC(CP(=O)(OCC)OCC)=CC=3)N=2)=C2C=1CN(C)C2=O.CN1CCNCC1>>[CH3:19][N:16]1[C:15](=[O:20])[C:14]2[C:18](=[C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH3:1])[CH2:5][CH2:6]3)[CH:11]=[CH:12][C:13]=2[NH:21][C:22]2[C:27]([C:28]([F:31])([F:29])[F:30])=[CH:26][N:25]=[C:24]([NH:32][C:33]3[CH:47]=[CH:46][C:36]([CH2:37][P:38](=[O:45])([O:39][CH2:40][CH3:41])[O:42][CH2:43][CH3:44])=[CH:35][CH:34]=3)[N:23]=2)[CH2:17]1

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-acetyl piperazin-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-0299938ecbd2483582cb0b4243c7b7c4
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

Loading…