Methyl chloroformate → {6-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridin-3-yl}-carbamic acid methyl ester

HRID 42217Notes

Reaction equation

HRID 42217 reaction equation
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:39]([O:41][CH3:42])=[O:40]>C(Cl)Cl>[CH3:42][O:41][C:39](=[O:40])[NH:30][C:27]1[CH:28]=[N:29][C:24]([N:21]2[CH2:20][CH2:19][N:18]([C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:9][N:10]=3)[CH2:23][CH2:22]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 592405406-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridin-3-ylamine

Product 1

HCID 59240657{6-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridin-3-yl}-carbamic acid methyl esterYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridin-3-ylamine (80 mg, 0.202 mmol), CH2Cl2 (0.5 mL), triethylamine (37 μL, 0.227 mmol), and methyl chloroformate (17 μL, 0.222 mmol) are combined and stirred at room temperature. Reaction complete in less than 15 minutes. Concentrate reaction mixture in vacuo. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (39 mg, 42%).

Workup

  1. customReaction complete in less than 15 minutes
  2. concentrationConcentrate
  3. customreaction mixture in vacuo
  4. customThe residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-76718e9f14fa4d8bab7a5c5347959b32
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

Loading…