Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → HCID 178476862, compound

HRID 1947833Notes

Reaction equation

HRID 1947833 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]=2OC)[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>>[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:10])[F:9])=[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][CH:14]=4)[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 178476862HCID 178476862, 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. 1H NMR (400 MHz, DMSO-d6) δ 10.57 (s, 1H), 9.87 (s, 1H), 8.45 (s, 1H), 7.56 (br. s., 1H), 7.38 (d, J=8.59 Hz, 1H), 7.26 (dd, J=2.15, 8.46 Hz, 2H), 4.58 (d, J=4.55 Hz, 1H), 4.52 (s, 2H), 3.91-4.01 (m, 4H), 3.46-3.54 (m, 1H), 3.17-3.27 (m, 2H), 3.08 (s, 3H), 1.94 (d, J=9.85 Hz, 2H), 1.76 (d, J=12.13 Hz, 2H), 1.53-1.65 (m, 2H), 1.23-1.36 (m, 2H), 1.18 (t, J=7.07 Hz, 6H). MS (ES+): m/z: 648.1830 [MH+]. HPLC: tR=1.44 min (UPLC TOF MS: polar—3 min).

Workup

  1. customPurification
  2. washISCO Combi-flash Rf system, eluting with 0 to 5% MeOH in EtOAc
  3. customHPLC: tR=1.44 min (UPLC TOF MS: polar—3 min)

Sources & evidence

ORD record
ord-72e2ab83a24a485fb050b9de50079cad
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

Loading…