Diisopropylethylamine → HCID 67442263, compound

HRID 2045673Notes

Reaction equation

HRID 2045673 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=2)[NH:9]1.C(N(CC)C(C)C)(C)C.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](Cl)=[O:40]>ClCCl>[CH3:19][C:17]1([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=2)[NH:9][CH:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:39](=[O:40])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 67441977HCID 67441977, compound

Product 1

HCID 67442263HCID 67442263, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold mixture of methyl 2-(2-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (60 mg, 0.19 mmol, 1.0 eq.) and N,N-diisopropylethylamine (50 mg, 0.38 mmol, 2.0 eq.) in 4 mL of dichloromethane was added dropwise a solution of picolinoyl chloride (40 mg, 0.29 mmol, 1.5 eq.) in dichloromethane (1 mL). Then the resultant mixture was stirred at room temperature for 30 min. Thin layer chromatography and LC-MS indicated that the starting material was consumed completely. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=2:1) to afford 44 mg of methyl 3,3-dimethyl-2-(2-(picolinamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate as a gray solid; yield: 60%. MS (ESI+APCI) M+1=416.2.

Workup

  1. customwas consumed completely
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-614386aebe224ae8ae449a4714c4299b
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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