Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → HCID 178472346, compound

HRID 1947830Notes

Reaction equation

HRID 1947830 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]([C@H:42]2[CH2:47][CH2:46][C@H:45]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:44][CH2:43]2)=[C:35]2[C:39]=1[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]2>>[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:30][C:31]3[CH:32]=[CH:33][C:34]([C@H:42]4[CH2:43][CH2:44][C@H:45]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:46][CH2:47]4)=[C:35]4[C:39]=3[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]4)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[C:14]([O:28][CH3:29])[CH:15]=1)([O:22][CH2:23][CH3:24])=[O:25])[CH3:21]

Participants

3

Reactant 2

HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 178472342HCID 178472342, compound

Product 1

HCID 178472346HCID 178472346, compound

Procedure

This compound was prepared in a manner analogous to Example 87 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and ethyl trans-4-(7-amino-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl)cyclohexanecarboxylate. 1H NMR (400 MHz, MeOD) δ ppm 8.51 (d, J=8.84 Hz, 1H), 8.36 (s, 1H), 7.89 (d, J=8.08 Hz, 1H), 7.40 (d, J=8.84 Hz, 1H), 7.08 (t, J=2.02 Hz, 1H), 6.97 (dt, 1H), 4.53 (s, 2H), 4.06-4.20 (m, 6H), 3.92 (s, 3H), 3.35-3.36 (m, 1H), 3.29-3.31 (m, 1H), 3.20 (s, 3H), 2.44-2.68 (m, 2H), 2.14 (d, J=10.61 Hz, 2H), 1.91-1.98 (m, 2H), 1.57-1.77 (m, 4H), 1.30 (q, 9H). MS (ES+): m/z=734.84 [MH+]. HPLC: tR=1.74 min (UPLC TOF, polar—3 min).

Workup

  1. customHPLC: tR=1.74 min (UPLC TOF, polar—3 min)

Sources & evidence

ORD record
ord-34aceb59676746beb1fa5502dd47b15f
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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