Dimethylformamide → HCID 16123906, compound

HRID 886801Notes

Reaction equation

HRID 886801 reaction equation
C([CH:3]1[C:12]2[N:11]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[N:9]=C(C)[C:7]=2N=[C:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:4]1=O)C.Cl.Cl[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.[C:39]([O-])([O-])=O.[K+].[K+].[CH3:45][N:46]([CH:48]=[O:49])[CH3:47]>>[CH2:45]([N:46]1[C:47]2[N:9]=[C:10]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH2:31][CH2:32][N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:18][CH:19]=3)[N:11]=[C:12]([CH3:7])[C:3]=2[CH:4]=[C:5]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:48]1=[O:49])[CH3:39]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 86628417HCID 86628417, compound

Product 1

HCID 16123906HCID 16123906, compoundYield 77%

Procedure

8-Ethyl-2-(4-hydroxyphenylamino)-4-methyl-6-phenylpyrido[2,3-]pyrimidin-7(8H)-one (70 mg, 0.188 mmol) from above, 1-(2-chloroethyl)piperidine hydrochloride (245.0 mg, 1.331 mmol) and K2CO3 (450.0 mg, 3.261 mmol) were added to DMF (5 mL). The reaction was heated to reflux for ten minutes then cooled to room temperature and partitioned between aqueous and organic layers with ethyl acetate and H2O. The organic layer was dried with anhydrous magnesium sulfate, filtered and evaporated. The residue was directly applied to prep-LC to provide 8-Ethyl-4-methyl-6-phenyl-2-({4-[(2-piperidin-1-ylethyl)oxy]phenyl}amino)pyrido[2,3-d]pyrimidin-7(8H)-one (17.0 mg, 77% yield): 1H NMR (400 MHz, DMSO-d6): δ 10.00 (bs, 1H), 8.10 (s, 1H), 7.70 (m, 4H), 7.40 (m, 3H), 6.95 (d, 2H), 4.40 (q, 2H), 4.10 (bs, 2H), 3.40 (bs, 6H), 2.60 (s, 3H), 1.60 (bs, 4H), 1.40 (bs, 2H), 1.23 (t, 3H); MS (EI) for C29H33N5O2: 484.1 (MH+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for ten minutes
  3. custompartitioned between aqueous and organic layers with ethyl acetate and H2O
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-34af895f30e24e4bbf7c04ddeaea6820
Source dataset
uspto-grants-2012_08
Patent number
US08247408B2

Reaction notes

Loading…