2-{4-[(R)-3-(2,4-Dimethyl-phenoxy)-2-hydroxy-propylamino]-6-oxo-1,6-dihydro-pyrimidin-5-yl}-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione → HCID 178426859, compound

HRID 561932Notes

Reaction equation

HRID 561932 reaction equation
[CH3:1][C:2]1[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][C:3]=1[O:4][CH2:5][C@H:6]([OH:37])[CH2:7][NH:8][C:9]1[N:10]=[CH:11][NH:12][C:13](=[O:36])[C:14]=1[C:15]1[NH:16][C:17]2[C:25]([N:26]=1)=[CH:24][C:23]1[C:22](=[O:27])[N:21]([CH:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[C:20](=O)[C:19]=1[CH:18]=2>CC(O)=O.[Zn]>[CH3:1][C:2]1[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][C:3]=1[O:4][CH2:5][C@H:6]([OH:37])[CH2:7][NH:8][C:9]1[NH:10][CH2:11][NH:12][C:13](=[O:36])[C:14]=1[C:15]1[NH:26][C:25]2[C:17](=[CH:18][C:19]3[CH2:20][N:21]([CH:28]4[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]4)[C:22](=[O:27])[C:23]=3[CH:24]=2)[N:16]=1

Participants

4

Reactant 1

HCID 1362001702-{4-[(R)-3-(2,4-Dimethyl-phenoxy)-2-hydroxy-propylamino]-6-oxo-1,6-dihydro-pyrimidin-5-yl}-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione

Product 1

HCID 178426859HCID 178426859, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

2-{4-[(R)-3-(2,4-Dimethyl-phenoxy)-2-hydroxy-propylamino]-6-oxo-1,6-dihydro-pyrimidin-5-yl}-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione (60.1 mg, 0.105 mmol) was mixed with zinc dust (300 mg) in AcOH (12 mL) resulting a mixture which was heated at 90° C. for 1 h, then cooled to the room temperature and filtered. The filtrate was evaporated, the residue was basified with NH3 in EtOH (2 M) and purified by chromatography with CH2Cl2/MeOH/28% aqueous NH4OH (60:10:1) to furnish a fluorescent product which was subjected to HPLC purification to afford the title compound in TFA salt form (42 mg, 60%). 1H NMR (DMSO-d6) δ 1.90-2.15 (4H), 2.13 (s, 3H, CH3), 2.20 (s, 3H, CH3), 2.81 (s, 3H, CH3), 3.20 (m, 2H), 3.40-3.60 (4H), 3.97 (m, 2H), 4.13 (m, 1H), 4.31 (m, 1H), 4.40 (s, 2H), 4.46 (s, 2H), 6.83 (d, J=6 Hz, 1H), 6.93 (d, J=6 Hz, 1H), 6.96 (s, 1H), 7.53 (br s, 1H), 7.75 (s, 1H), 9.75 (br s, 1H); ESI-MS m/z 560.5 (MH+).

Workup

  1. customresulting a mixture which
  2. temperaturecooled to the room temperature
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. custompurified by chromatography with CH2Cl2/MeOH/28% aqueous NH4OH (60:10:1)
  6. customto furnish a fluorescent product which
  7. customwas subjected to HPLC purification

Sources & evidence

ORD record
ord-0ad1b921fa624854ab47815da9ec1086
Source dataset
uspto-grants-2011_11
Patent number
US08063225B2

Reaction notes

Loading…