Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → HCID 178476866, compound

HRID 1947835Notes

Reaction equation

HRID 1947835 reaction equation
[Cl:1][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]([OH:48])[CH2:44][CH2:43]2)=[C:35]2[C:39]=1[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]2>>[ClH:1].[OH:48][C@H:45]1[CH2:46][CH2:47][C@H:42]([C:34]2[CH:33]=[CH:32][C:31]([NH:30][C:2]3[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][N:5]=[C:4]([NH:12][C:13]4[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]=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])[CH2:43][CH2:44]1

Participants

3

Reactant 2

HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 178479967HCID 178479967, compound

Product 1

HCID 178476866HCID 178476866, 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 7-amino-4-(trans-4-hydroxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one. Purification: ISCO Combi-flash RF system eluting with 0 to 5% MeOH in EtOAc. The pure product was dissolved in 1 mL of 12M HCl then concentrated in vacuo to afford the title compound as the HCl Salt: 1H NMR (400 MHz, DMSO-d6) δ10.60 (s, 1H), 9.10 (br. s., 1H), 8.37 (s, 1H), 7.43 (br. s., 1H), 7.31 (d, J=8.59 Hz, 1H), 7.07 (s, 1H), 6.92 (d, J=7.83 Hz, 1H), 4.48 (s, 2H), 3.92-4.05 (m, 7H), 3.44-3.56 (m, 1H), 3.23-3.35 (m, 2H), 3.06 (s, 3H), 1.92 (d, J=10.36 Hz, 2H), 1.54-1.75 (m, 4H), 1.23-1.33 (m, 2H), 1.19 (t, J=7.07 Hz, 6H). MS (ES+): m/z: 678.24 [MH+]. HPLC: tR=3.37 min (Micromass ZQ3: polar—5 min).

Workup

  1. customPurification
  2. washISCO Combi-flash RF system eluting with 0 to 5% MeOH in EtOAc
  3. dissolutionThe pure product was dissolved in 1 mL of 12M HCl
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-328b875be36044eca897755a1e7e96e8
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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