Anthranilic Acid → HCID 58293009, compound

HRID 1948101Notes

Reaction equation

HRID 1948101 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.[C:30]([OH:39])(=[O:38])[C:31]1[C:32](=[CH:34][CH:35]=[CH:36][CH:37]=1)[NH2:33]>>[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:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[C:30]([OH:39])=[O:38])[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 227Anthranilic AcidHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 58293009HCID 58293009, compound

Procedure

The title compound was prepared according to the procedure for example 102 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (50.0 mg, 0.110 mmol) and anthranilic acid (15.1 mg, 0.110 mmol). The reaction mixture concentrated under reduced pressure and purified on an ISCO Combiflash system (DCM/MeOH 100:0→95:5) twice. 1H NMR (400 MHz, CHLOROFORM-d) δ 11.65 (br. s., 1H), 9.74 (s, 1H), 8.48 (d, J=8.84 Hz, 1H), 8.25 (s, 1H), 8.08 (dd, J=1.39, 7.96 Hz, 1H), 7.81 (br. s., 1H), 7.47 (t, J=7.71 Hz, 1H), 7.12 (t, J=7.58 Hz, 1H), 6.94 (s, 1H), 6.88 (dd, J=2.02, 8.08 Hz, 1H), 4.06-4.17 (m, 4H), 3.85 (s, 3H), 3.18-3.29 (m, 2H), 1.30 (t, J=7.07 Hz, 6H). MS (ES+): m/z 555.1432 (MH+). HPLC: tR=1.47 min (UPLC TOF, polar—3 min).

Workup

  1. concentrationThe reaction mixture concentrated under reduced pressure
  2. custompurified on an ISCO Combiflash system (DCM/MeOH 100:0→95:5) twice
  3. customHPLC: tR=1.47 min (UPLC TOF, polar—3 min)

Sources & evidence

ORD record
ord-16faec183f704f42b0a96b09d6414de2
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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