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 511484Notes

Reaction equation

HRID 511484 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=2[O:28][CH3:29])[N:3]=1.[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>>[CH2:50]([N:48]([CH3:49])[CH:45]1[CH2:44][CH2:43][CH:42]([C:34]2[CH:33]=[CH:32][C:31]([NH:30][C:2]3[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]4[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24])=[CH:15][C:14]=4[O:28][CH3:29])[N:3]=3)=[C:39]3[C:35]=2[CH2:36][N:37]([CH3:41])[C:38]3=[O:40])[CH2:47][CH2:46]1)[CH3:51]

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, 6 H) 1.39 (t, J=7.33 Hz, 3 H) 1.70-1.86 (m, 4 H) 2.04 (br. s., 2 H) 2.19 (d, J=7.83 Hz, 2 H) 2.71 (br. s., 1 H) 2.86 (s, 3 H) 3.17-3.19 (m, 3 H) 3.33 (s, 1 H) 3.34-3.37 (m, 2 H) 3.39 (s, 1 H) 3.43-3.52 (m, 1 H) 3.89 (s, 3 H) 4.05-4.14 (m, 4 H) 4.55 (s, 2 H) 7.01 (dt, J=8.02, 2.31 Hz, 1 H) 7.15 (t, J=2.02 Hz, 1 H) 7.42 (d, J=8.34 Hz, 1 H) 7.57 (d, J=8.08 Hz, 1 H) 8.36 (br. s., 1 H). 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-adc193d8b02847019380e749422d095d
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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