7-amino-4-{4-[ethyl(methyl)amino]cyclohexyl}-2-methyl-2,3-dihydro-1H-isoindol-1-one → Diethyl[4-({4-[(7-{4-[ethyl(methyl)amino]cyclohexyl}-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)-3-methoxybenzyl]phosphonate

HRID 1948052Notes

Reaction equation

HRID 1948052 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](Cl)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)=[C:12]([O:28][CH3:29])[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([CH:42]2[CH2:47][CH2:46][CH:45]([N:48]([CH2:50][CH3:51])[CH3:49])[CH2:44][CH2:43]2)=[C:35]2[C:39]=1[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]2>>[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:30][C:31]3[CH:32]=[CH:33][C:34]([CH:42]4[CH2:43][CH2:44][CH:45]([N:48]([CH2:50][CH3:51])[CH3:49])[CH2:46][CH2:47]4)=[C:35]4[C:39]=3[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]4)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)=[C:12]([O:28][CH3:29])[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

3

Reactant 2

HCID 672557897-amino-4-{4-[ethyl(methyl)amino]cyclohexyl}-2-methyl-2,3-dihydro-1H-isoindol-1-one2×HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 58293054Diethyl[4-({4-[(7-{4-[ethyl(methyl)amino]cyclohexyl}-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)-3-methoxybenzyl]phosphonate

Procedure

This compound was prepared according to the procedure for Example 102 using diethyl(4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and 7-amino-4-{4-[ethyl(methyl)amino]cyclohexyl}-2-methyl-2,3-dihydro-1H-isoindol-1-one (Compound 236A). 1H NMR (400 MHz, MeOD) δ ppm 1.28 (t, J=7.07 Hz, 6H) 1.39 (t, J=7.33 Hz, 3H) 1.70-1.86 (m, 4H) 2.04 (br. s., 2H) 2.19 (d, J=7.83 Hz, 2H), 2.71 (br. s., 1H) 2.86 (s, 3H) 3.17-3.19 (m, 3H) 3.33 (s, 1H) 3.34-3.37 (m, 2H) 3.39 (s, 1H) 3.43-3.52 (m, 1H) 3.89 (s, 3H) 4.05-4.14 (m, 4H) 4.55 (s, 2H) 7.01 (dt, J=8.02, 2.31 Hz, 1H), 7.15 (t, J=2.02 Hz, 1H) 7.42 (d, J=8.34 Hz, 1H) 7.57 (d, J=8.08 Hz, 1H) 8.36 (br. s., 1H). MS (ES+): m/z 719.25/720.29 (100/20) [MH+]. HPLC: tR=1.17 min (UPLC TOF: polar—3 min).

Workup

  1. customThis compound was prepared
  2. customHPLC: tR=1.17 min (UPLC TOF: polar—3 min)

Sources & evidence

ORD record
ord-dd7f894ee1124a46af3e34247ad8b686
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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