Potassium Carbonate → HCID 69588692, compound

HRID 859144Notes

Reaction equation

HRID 859144 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[Cl:30].C([O-])([O-])=O.[K+].[K+].[C:37]([O:42][CH2:43][CH3:44])(=[O:41])[C:38]#[C:39][CH3:40]>CN(C=O)C.C(Cl)Cl>[Cl:30][C:23]1[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=1[C:16]1[N:15]2[N:14]=[C:39]([CH3:40])[C:38]([C:37]([O:42][CH2:43][CH3:44])=[O:41])=[C:20]2[CH:19]=[CH:18][C:17]=1[CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 867603371-Amino-2-(2-chloro-4-methoxyphenyl)-3-methylpyridinium 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 69588692HCID 69588692, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of crude 1-amino-2-(2-chloro-4-methoxyphenyl)-3-methylpyridinium 2,4,6-trimethylbenzenesulfonate (2.63 g, 5.9 mmol) in DMF (15 mL) was treated with K2CO3 (4.05 g, 29.3 mmol). A solution of ethyl but-2-ynoate (0.77 g, 6.9 mmol) in DMF (2 mL) was added and the reaction was stirred at ambient temperature for 16 hours then quenched with water and filtered to give a waxy yellow solid which was dissolved in CH2Cl2. The solution was washed with H2O, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo to give a yellow oil (1.02 g). The original aqueous filtrate from the reaction was concentrated in vacuo to remove DMF and partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 and the combined organic layers was dried over MgSO4, concentrated in vacuo, combined with the yellow oil and subjected to column chromatography (30% ethyl acetate/heptane) to give 0.89 g (42%) of a yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 8.09 (d, J=9.0 Hz, 1H), 7.38 (d, J=9.0 Hz, 1H), 7.28 (d, J=8.5 Hz, 1H), 7.15 (d, J=2.5 Hz, 1H), 7.04 (dd, J=8.5, 2.5 Hz, 1H), 4.42 (q, J=7.1 Hz, 2H), 3.92 (s, 3H), 2.63 (s, 3H), 2.17 (s, 3H), 1.46 (t, J=7.1 Hz, 3H); MS m/z 359.39 (M++H).

Workup

  1. customthen quenched with water
  2. filtrationfiltered
  3. customto give a waxy yellow solid which
  4. washThe solution was washed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7a8a97c082604e1bad00d2a873394f99
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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