4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 10193807, compound

HRID 2181438Notes

Reaction equation

HRID 2181438 reaction equation
[CH2:1]([C:4]1[CH:21]=[CH:20][C:7]([NH:8][C:9]2[C:17]([F:18])=[C:16]([F:19])[CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)=[C:6]([F:22])[CH:5]=1)[CH:2]=[CH2:3].[NH2:23][O:24][CH2:25][CH2:26][OH:27].[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO>[CH2:1]([C:4]1[CH:21]=[CH:20][C:7]([NH:8][C:9]2[C:17]([F:18])=[C:16]([F:19])[CH:15]=[CH:14][C:10]=2[C:11]([NH:23][O:24][CH2:25][CH2:26][OH:27])=[O:13])=[C:6]([F:22])[CH:5]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride2×HCID 3014186Ethanol, 2-(aminooxy)-HCID 22025610HCID 22025610, compound

Product 1

HCID 10193807HCID 10193807, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4-Allyl-2-fluoroanilino)-3,4-difluorobenzoic acid (700 mg, 2.28 mmol) was dissolved in MeOH (20 mL) to which was added 2-(aminooxy)ethanol (263 mg, 3.42 mmol), followed by 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methymorpholinium chloride [DMT-MM, prepared according to the procedure of Kunishima et al [Tetrahedron, 55, 13159-13170 (1999)]] (946 mg, 3.42 mmol). This mixture was stirred 15 h. at room temperature. The MeOH was removed under reduced pressure and the resulting oil dissolved in EtOAc (100 mL), which was washed with water (2×100 mL), brine (100 mL) and dried (Na2SO4). The solvent was removed under reduced pressure to afford a crude yellow oil which was purified by filtration through a plug of silica gel (50% EtOAc/PE as eluant) to give 2-(4-allyl-2-fluoroanilino)-3,4-difluoro-N-(2-hydroxyethoxy)benzamide as a white solid (734 mg, 88%); m.p. (EtOAc/hexane) 173-177° C. 1H NMR [400 MHz, (CD3)2SO] δ 11.85 (br s, 1 H), 8.75 (br s, 1 H), 7.43-7.37 (m, 1 H), 7.14-7.07 (m, 1 H), 7.05-6.99 (m, 1 H), 6.90-6.81 (m, 2 H), 5.99-5.87 (m, 1 H), 5.02-5.11 (m, 2 H), 4.70 (br s, 1 H), 3.85 (t, J=4.9 Hz, 1 H), 3.57 (t, J=4.9 Hz, 1 H), 3.51-3.40 (m, 2H, obscured by H2O). Anal. calcd. for C18H17F3N2O3: C, 59.0; H, 4.7; N, 7.7. Found C, 59.1; H, 4.5; N, 7.4.

Workup

  1. customprepared
  2. customThe MeOH was removed under reduced pressure
  3. dissolutionthe resulting oil dissolved in EtOAc (100 mL)
  4. washwhich was washed with water (2×100 mL), brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed under reduced pressure
  7. customto afford a crude yellow oil which
  8. filtrationwas purified by filtration through a plug of silica gel (50% EtOAc/PE as eluant)

Sources & evidence

ORD record
ord-ca972f458386419abf07550acf57b70b
Source dataset
uspto-grants-2005_05
Patent number
US06891066B2

Reaction notes

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