Methyl Acrylate → HCID 67143388, compound

HRID 574258Notes

Reaction equation

HRID 574258 reaction equation
[NH2:1][C@H:2]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:3][N:4]1[C:9](=[O:10])[C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)[CH2:13][CH2:12]2)=[C:7]([CH3:27])[N:6]([CH2:28][C:29]2[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][C:30]=2[F:39])[C:5]1=[O:40].[C:47]([O:51][CH3:52])(=[O:50])[CH:48]=[CH2:49]>CO>[CH3:52][O:51][C:47](=[O:50])[CH2:48][CH2:49][NH:1][C@H:2]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH2:3][N:4]1[C:9](=[O:10])[C:8]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)[CH2:15][CH2:16]2)=[C:7]([CH3:27])[N:6]([CH2:28][C:29]2[C:34]([C:35]([F:38])([F:36])[F:37])=[CH:33][CH:32]=[CH:31][C:30]=2[F:39])[C:5]1=[O:40]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 67142732HCID 67142732, compound

Product 1

HCID 67143388HCID 67143388, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a closed tube, 3-((R)-2-amino-2-phenyl-ethyl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-5-[4-(3-nitro-benzyl)-piperazin-1-yl]-1H-pyrimidine-2,4-dione (3-58) (20 mg, 0.031 mmol), methyl acrylate (9 μl, 0.093 mmol), and methanol (2 mL) were mixed at 70° C. for 4 hrs with stirring. The resulting solution was concentrated, and the residue was purified using silica gel chromatography (eluent: dichloromethane/methanol, 20/1) and dried in a vacuum to afford 17 mg of the compound as a colorless oil (yield 74%). 1H NMR (300 MHz, CDCl3) δ 2.17 (2H, m), 2.33 (3H, s), 2.38 (2H, t), 2.40-2.77 (6H, m), 3.58 (7H, m), 4.02-4.20 (3H, m), 5.39 (2H, d), 7.20-7.55 (9H, m), 7.77 (1H, d), 8.10 (1H, d), 8.17 (1H, s)

Workup

  1. concentrationThe resulting solution was concentrated
  2. customthe residue was purified
  3. customdried in a vacuum

Sources & evidence

ORD record
ord-954952c9e56044a7a4c795707e9007bc
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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