7-Amino-2,3,3-trimethyl-2,3-dihydro-1H-isoindol-1-one → Diethyl [3-methoxy-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 511364Notes

Reaction equation

HRID 511364 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][CH:34]=[C:35]2[C:39]=1[C:38](=[O:40])[N:37]([CH3:41])[C:36]2([CH3:43])[CH3:42]>>[CH3:29][O:28][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:13]=1[NH:12][C:4]1[N:3]=[C:2]([NH:30][C:31]2[CH:32]=[CH:33][CH:34]=[C:35]3[C:39]=2[C:38](=[O:40])[N:37]([CH3:41])[C:36]3([CH3:42])[CH3:43])[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=1)[CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 672553277-Amino-2,3,3-trimethyl-2,3-dihydro-1H-isoindol-1-one2×HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 58292931Diethyl [3-methoxy-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}-3-methoxybenzyl)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: 9.00 (br s, 1H), 8.33 (s, 1H), 7.92 (s, 1H), 7.38-7.45 (m, 1H), 7.32 (br s, 1H), 7.07-7.16 (m, 2H), 6.84 (s, 1H), 6.31 (br s, 1H), 3.91 (quin, J=7.3 Hz, 4H), 3.77 (s, 3H), 3.13 (s, 3H), 3.06 (d, J=21.2 Hz, 2H), 1.27 (s, 6H), 1.16 (t, J=7.1 Hz, 6H). MS (ES+): m/z 608.24 [MH+] HPLC: tR=1.31 min (UPLC, analytical).

Sources & evidence

ORD record
ord-7f9793fa2f26496fb91403d8cad81e06
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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