Ethyl Acetate → HCID 66977297, compound

HRID 712357Notes

Reaction equation

HRID 712357 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:6][C:5]([C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:25][CH2:24][C:23]([CH2:31][CH3:32])([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]3)=[N:18][CH:19]=2)=[CH:4][C:3]=1[N+:33]([O-])=O.CCOC(C)=O>[Pd]>[NH2:33][C:3]1[CH:4]=[C:5]([C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:25][CH2:24][C:23]([CH2:31][CH3:32])([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]3)=[N:18][CH:19]=2)[CH:6]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 66977115HCID 66977115, compound

Product 1

HCID 66977297HCID 66977297, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of ethyl 1-(5-(4-amino-3-nitro-5-(pyridin-2-yl)phenyl)pyrimidin-2-yl)-4-ethylpiperidine-4-carboxylate (0.70 g, 1.46 mmol) in EtOAc (20.0 mmol) was added Pd/C (0.14 g, 20% w/w) and the mixture stirred at rt under hydrogen for 16 h. After completion the reaction (by TLC), the mixture was filtered through celite, the filtrate concentrated under reduced pressure and triturated with Et2O to afford the desired product (0.65 g, 99%). 1H NMR (DMSO-d6): δ 8.61-8.62 (m, 1H), 8.58 (s, 2H), 7.86-7.88 (m, 2H), 7.28-7.30 (m, 1H), 7.11 (s, 1H), 6.84 (s, 1H), 6.16 (s, 2H), 4.78 (br s, 2H), 4.38-4.42 (m, 2H), 4.13-4.18 (m, 2H), 3.04-3.10 (m, 2H), 2.04-2.08 (m, 2H), 1.55-1.57 (m, 2H), 1.37-1.39 (m, 2H), 1.19 (t, J=7.20 Hz, 3H) and 0.83 (t, J=7.20 Hz, 3H). MS: 447.35 [M+H]+

Workup

  1. customAfter completion the reaction (by TLC)
  2. filtrationthe mixture was filtered through celite
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customtriturated with Et2O

Sources & evidence

ORD record
ord-9f959726adce44daaeeadf09df480dc1
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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