Methyl chloroformate → HCID 53237107, compound

HRID 407193Notes

Reaction equation

HRID 407193 reaction equation
[C:1]([C:3]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([C:21]([NH:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[O:22])[C:13](=[O:20])[N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH2:5][CH2:4]1)#[N:2].C(N(CC)CC)C.Cl[C:44]([O:46][CH3:47])=[O:45]>ClCCl>[C:1]([C:3]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([C:21]([NH:23][CH:24]3[CH2:29][CH2:28][N:27]([C:44]([O:46][CH3:47])=[O:45])[CH2:26][CH2:25]3)=[O:22])[C:13](=[O:20])[N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 86670625HCID 86670625, compound

Product 1

HCID 53237107HCID 53237107, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[(4-cyano-4-pyridin-2-ylpiperidin-1-yl)methyl]-4-oxo-N-piperidin-4-yl-4H-quinolizine-3-carboxamide (0.027 g, 0.057 mmol) in 2 mL of dichloromethane was added triethylamine (0.3 mL, 2.1 mmol) followed by methyl chloroformate (0.10 mL, 1.3 mmol). After 1 h, the mixture was washed with 0.5 N aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title compound that gave a proton NMR spectra consistent with theory: 1H NMR (400 MHz, CDCl3) δ 9.80 (d, J=7.7 Hz, 1H), 9.40 (d, J=7.3 Hz, 1H), 8.65 (s, 1H), 8.60-8.58 (m, 1H), 8.19 (d, J=8.9 Hz, 1H), 7.76-7.66 (m, 2H), 7.62-7.59 (m, 1H), 7.32-7.23 (m, 2H), 4.24-4.21 (m, 1H), 4.03 (br s, 1H), 3.82 (s, 2H), 3.71 (s, 3H), 3.69-3.61 (m, 2H), 3.15-3.09 (m, 1H), 3.02-2.98 (m, 1H), 2.60-2.57 (m, 1H), 2.55-2.50 (m, 2H), 2.32-2.25 (m, 1H), 2.09-2.02 (m, 2H), 1.93 (br s, 1H), 1.59-1.52 (m, 1H), 1.40-1.37 (m, 2H), 1.06-1.01 (m, 3H).

Workup

  1. washthe mixture was washed with 0.5 N aqueous sodium hydroxide and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b27289a8e6a843798dcee678665dcea2
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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