Triethylamine → 4-[6-bromo-2-(methoxymethyl)-1H-1,3-benzodiazol-1-yl]-1,3,5-triazin-2-amine

HRID 1398708Notes

Reaction equation

HRID 1398708 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[N:15]=[C:14]([NH2:16])[N:13]=[CH:12][N:11]=1.[CH3:17][O:18][CH2:19][C:20](O)=O.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:20]([CH2:19][O:18][CH3:17])[N:9]([C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:16])[N:15]=3)[C:3]=2[CH:4]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 12251Methoxyacetic AcidHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 681816982-N-(2-amino-5-bromophenyl)-1,3,5-triazine-2,4-diamine

Product 1

HCID 681816384-[6-bromo-2-(methoxymethyl)-1H-1,3-benzodiazol-1-yl]-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-N-(2-amino-5-bromophenyl)-1,3,5-triazine-2,4-diamine (1.00 g, 3.56 mmol) in DMF (5 mL) was introduced methoxyacetic acid (320 mg, 3.56 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (750 mg, 3.91 mmol), 1-hydroxy-7-azabenzotriazole (533 mg, 3.91 mmol) and triethylamine (720 mg, 7.11 mmol). The reaction mixture was stirred for 18 hr at RT and concentrated in vacuo. The residue was suspended in water (100 mL) and the resulting precipitate collected by filtration. After washing the filter cake with EtOAc (10 mL) and methanol (10 mL), the crude amide was dried on the filter. The intermediate amide was dissolved in glacial acetic acid (20 mL) and warmed to 140° C. for 15 minutes (microwave heating in 4 batches of equal volume). Following concentration of the reaction mixture in vacuo, toluene (20 mL) was introduced and the suspension concentrated in vacuo (repeated twice) to furnish the crude title compound as a brown oil: LC-MS: m/z=+334.90/336.75 (M+H)+. This compound, with LC-MS purity=86% UV, was used in the next step without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationthe resulting precipitate collected by filtration
  3. washAfter washing the filter cake with EtOAc (10 mL) and methanol (10 mL)
  4. dry with materialthe crude amide was dried on the filter
  5. dissolutionThe intermediate amide was dissolved in glacial acetic acid (20 mL)
  6. temperaturewarmed to 140° C. for 15 minutes
  7. temperature(microwave heating in 4 batches of equal volume)
  8. additionwas introduced
  9. concentrationthe suspension concentrated in vacuo (

Sources & evidence

ORD record
ord-fed63e8a6f4a41f4b1970b7ba901ddae
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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