Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → HCID 178476849, compound

HRID 1948125Notes

Reaction equation

HRID 1948125 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[C:36]2[C:37](=[O:41])[N:38]([CH3:40])[CH2:39][C:35]=2[CH:34]=[CH:33][N+:32]=1[O-:42]>>[CH2:23]([O:22][P:18]([CH2:17][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:30][C:31]3[C:36]4[C:37](=[O:41])[N:38]([CH3:40])[CH2:39][C:35]=4[CH:34]=[CH:33][N+:32]=3[O-:42])[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][N:5]=2)=[CH:27][CH:26]=1)(=[O:25])[O:19][CH2:20][CH3:21])[CH3:24]

Participants

3

Reactant 2

HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 178479968HCID 178479968, compound2×

Product 1

HCID 178476849HCID 178476849, 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 (204 mg, 0.381 mmol) and 4-amino-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one 5-oxide (Compound 310A, 68.3 mg, 0.381 mmol). The reaction mixture was concentrated under reduced pressure to yield a dark yellow oil which was purified by silica gel chromatography on the combi-flash Rf system using DCM/MeOH (100:0→90:10). The fractions containing product were combined and concentrated under reduced pressure to yield a white solid (38.4 mg, 17%). 1H NMR (DMSO-d6, 400 MHz): δ=8.99 (br. s., 1H), 8.47-8.55 (m, 3H), 7.47 (d, J=6.57 Hz, 1H), 7.24 (d, J=7.58 Hz, 1H), 6.85 (s, 1H), 6.56 (d, J=8.08 Hz, 1H), 4.45 (s, 2H), 3.90-3.99 (m, 4H), 3.70 (s, 3H), 3.12-3.21 (m, 2H), 2.86-2.89 (m, 3H), 1.17 (t, J=7.07 Hz, 6H). MS (ES+): m/z 597.10 [MH+] (TOF, polar).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto yield a dark yellow oil which
  3. customwas purified by silica gel chromatography on the combi-flash Rf system
  4. additionThe fractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8241e8a95c7c4933b16b2d08d8467800
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

Loading…