Triethylamine → HCID 59294488, compound

HRID 1877436Notes

Reaction equation

HRID 1877436 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]([CH:30]4[CH2:32][CH2:31]4)[CH2:22][CH2:21]3)=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=2)[C:8]([Cl:33])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[CH3:66][O:67][C:68](=[O:71])[CH2:69][NH2:70].C([O-])(O)=O.[Na+]>ClCCl>[CH3:66][O:67][C:68](=[O:71])[CH2:69][NH:70][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Cl:33])[C:9]([O:11][C:12]2[C:17]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]([CH:30]4[CH2:31][CH2:32]4)[CH2:22][CH2:21]3)=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:10][C:2]=1[Cl:1]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67367161HCID 67367161, compound

Product 1

HCID 59294488HCID 59294488, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-2-yloxy]-benzoic acid (38 mg, 0.079 mmol, 1.0 equiv) in dichloromethane (1.5 mL) was added HATU (38.8 mg, 0.10 mmol, 1.3 equiv; [CAS RN 148893-10-1]) and triethylamine (16 mg, 22 μL, 0.16 mmol, 2.0 equiv; [CAS RN 121-44-8]). After stirring the reaction mixture for 15 min, glycine methyl ester hydrochloride (12.8 mg, 0.10 mmol, 1.3 equiv; [CAS RN 5680-79-5]) was added and stirring continued at rt for 4 h. The crude reaction product was taken up in a sat. solution of NaHCO3 (50 mL) and extracted with dichloromethane (3×40 mL). The combined organic phases were dried over MgSO4 and the product purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate to give 43 mg (99%) of the title compound as a light yellow viscous oil. MS (ISN): 555.3 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued at rt for 4 h
  3. customThe crude reaction product
  4. extractionextracted with dichloromethane (3×40 mL)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. customthe product purified by silica column chromatography
  7. washeluting with a gradient of heptane/ethyl acetate

Sources & evidence

ORD record
ord-5edeb0bd128043e1a474911073427cba
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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