Triethylamine → HCID 178501231, compound

HRID 75516Notes

Reaction equation

HRID 75516 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1)=[O:4].CCN(CC)CC.[Cl:19][C:20]1[CH:21]=[N:22][C:23]([CH3:29])=[C:24]([CH:28]=1)[C:25](Cl)=[O:26]>C1COCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:25]([C:24]2[C:23]([CH3:29])=[N:22][CH:21]=[C:20]([Cl:19])[CH:28]=2)=[O:26])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 532566655-Chloro-2-methylnicotinoyl chloride2×HCID 178501207HCID 178501207, compound

Product 1

HCID 178501231HCID 178501231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trans-4-Amino-cyclohexanecarboxylic acid methyl ester (2.14 g, 11.05 mmol) was suspended in THF (50 ml) and Et3N (2.79 g, 27.6 mmol) and cooled to 0° C. 5-Chloro-2-methylnicotinoyl chloride (Intermediate C) (2.20 g, 11.05 mmol) was slowly added portionwise and the reaction mixture was stirred at RT for 2 hours. The reaction mixture was partitioned between EtOAc and 1M HCl. The organic phase was washed with water, brine, dried over MgSO4, filtered and the solvent was removed in vacuo to afford the title product which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (1H, d), 7.42 (1H, 5), 7.80 (1H, d), 3.70 (1H, m), 3.60 (3H, s), 2.49 (3H, s), 2.29 (1H, m), 1.95 (4H, m), 1.42 (2H, m), 1.29 (2H, m); [M+H]+311.26.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and 1M HCl
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aa0407480a714ebbb9501ffac14f116e
Source dataset
uspto-grants-2014_09
Patent number
US08835444B2

Reaction notes

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