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

HRID 1947936Notes

Reaction equation

HRID 1947936 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][CH:14]=2)[N:3]=1.[NH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]2[C:37]=1[C:36](=[O:38])[N:35]([CH3:39])[C:34]2([CH3:41])[CH3:40]>>[CH2:20]([O:19][P:18]([CH2:17][C:16]1[CH:26]=[CH:27][C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:28][C:29]3[CH:30]=[CH:31][CH:32]=[C:33]4[C:37]=3[C:36](=[O:38])[N:35]([CH3:39])[C:34]4([CH3:40])[CH3:41])[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][CH:15]=1)(=[O:25])[O:22][CH2:23][CH3:24])[CH3:21]

Participants

3

Reactant 2

HCID 672553277-Amino-2,3,3-trimethyl-2,3-dihydro-1H-isoindol-1-one2×HCID 86654003Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Product 1

HCID 58293002Diethyl [4-({5-(trifluoromethyl)-4-[(1,1,2-trimethyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]pyrimidin-2-yl}amino)benzyl]phosphonate

Procedure

The title compound was prepared according to the procedure from Example 102 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate and 7-Amino-2,3,3-trimethyl-2,3-dihydro-1H-isoindol-1-one (Compound 148A). 1H NMR (400 MHz, DMSO-d6) δ ppm: 9.71 (br s, 1H), 8.94 (br s, 1H), 8.35 (s, 1H), 7.43 (dd, J=6.2, 1.9 Hz, 1H), 7.06-7.30 (m, 4H), 6.80 (br s, 2H), 3.80-3.95 (m, 4H), 3.13 (s, 3H), 3.01 (d, J=21.5 Hz, 2H), 1.27 (s, 6H), 1.14 (t, J=7.1 Hz, 6H). MS (ES+): m/z 578.16 [MH+] HPLC: tR=3.27 min (ZQ3, polar—5 min).

Workup

  1. custom5 min

Sources & evidence

ORD record
ord-24da9ac8b1654acbb1fbf000ffcad9a6
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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