Ethylamine → HCID 69938867, compound

HRID 1619383Notes

Reaction equation

HRID 1619383 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:23]=[CH:22][N:13]3[C:14](=[O:21])[C:15]([C:18](O)=[O:19])=[CH:16][N:17]=[C:12]3[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:24][CH2:25][N:26](CC)CC.ClC(OCC)=O.C(N)C>C(Cl)(Cl)Cl>[CH2:25]([NH:26][C:18]([C:15]1[C:14](=[O:21])[N:13]2[CH:22]=[CH:23][C:10]([C:9]#[C:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[CH:11][C:12]2=[N:17][CH:16]=1)=[O:19])[CH3:24]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 58574452HCID 58574452, compound

Product 1

HCID 69938867HCID 69938867, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 8-((3-fluorophenyl)ethynyl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid (50 mg, 0.62 mmol, 1 equiv) and Et3N (0.5 mL) in CHCl3 (20 mL) at 0° C. was added ethyl chloroformate (0.4 mL) dropwise. After the reaction mixture was stirred for 10 min, aq. ethanamine (3 mL) was added. Then the mixture was stirred for 10 min and extracted with CHCl3 (3×30 mL), dried over Na2SO4 and concentrated to give the desired product (30 mg). MS (ESI): 336 (MH+); 1H NMR (300 MHz, CDCl3) δ 9.37 (s, 1H), 9.17-9.14 (d, J=7.32 Hz, 1H), 8.96-8.95 (m, 1H), 7.91 (s, 1H), 7.44-7.40 (m, 2H), 7.37-7.31 (m, 2H), 7.23-7.18 (m, 1H), 3.60-3.50 (m, 2H), 1.32-1.27 (t, J=7.2 Hz, 3H). mGluR5 PAM EC50: ++++.

Workup

  1. stirringThen the mixture was stirred for 10 min
  2. extractionextracted with CHCl3 (3×30 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-97cb784d4cc74b4b9de5ad55461cfdf1
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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