Water → HCID 90318585, compound

HRID 2280568Notes

Reaction equation

HRID 2280568 reaction equation
[Cl:1][C:2]1[C:3]([C:12](Cl)=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:15][C:16]1[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:18][CH:17]=1.N1C=CC=CC=1.O>ClCCl>[Cl:1][C:2]1[C:3]([C:12]([NH:15][C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:18][CH:17]=2)=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 19995701HCID 19995701, compound

Product 1

HCID 90318585HCID 90318585, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroquinoxaline-2-carbonyl chloride (1.0 g, 4.40 mmol) in dichloromethane (9.2 mL) was added dropwise to a mixture of tert-butyl 4-aminobenzoate (851.0 mg, 4.40 mmol), pyridine (1.07 mL, 13.21 mmol) and dichloromethane (13.8 mL) at 0° C. The reaction was stirred and allowed to warm up to room temperature over 40 minutes. To the reaction, water (10 mL) was added. The two layers were separated. The organic layer was washed with water (2×10 mL), dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The product was slurried in hexanes at 40° C., and the solid was isolated by filtration to yield tert-butyl 4-[(3-chloroquinoxaline-2-carbonyl)amino]benzoate (1.34 g, 79%) as a yellow solid. ESI-MS m/z calc. 383.10, found 384.4 (M+1)+; Retention time: 1.88 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 11.28 (s, 1H), 8.27 (dd, J=7.5, 2.1 Hz, 1H), 8.22-8.11 (m, 1H), 8.11-8.01 (m, 2H), 7.97 (d, J=8.8 Hz, 2H), 7.86 (d, J=8.7 Hz, 2H), 1.56 (s, 9H) ppm.

Workup

  1. additionwas added
  2. customThe two layers were separated
  3. washThe organic layer was washed with water (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customwas slurried in hexanes at 40° C.
  8. customthe solid was isolated by filtration

Sources & evidence

ORD record
ord-cc036199ed094902a3d40f6815a6e503
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

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