4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 10126289, compound

HRID 1793031Notes

Reaction equation

HRID 1793031 reaction equation
[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][C:14]=2[F:22])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.[NH2:23][O:24][CH2:25][CH2:26][OH:27].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CO>[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][C:14]=2[F:22])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([NH:23][O:24][CH2:25][CH2:26][OH:27])=[O:7]

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 3014186Ethanol, 2-(aminooxy)-HCID 22025674HCID 22025674, compound

Product 1

HCID 10126289HCID 10126289, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,4-Difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]benzoic acid was dissolved in MeOH and prepared from reaction with 2(aminooxy)ethanol and DMT-MM by the general procedure of Example 6, Step B, affording a crude yellow oil after workup which was purified by filtration through a plug of silica gel (100% EtOAc as eluant). 3,4-Difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]-N-(2-hydroxyethoxy)benzamide was isolated as a viscous, transparent oil (57%). 1H NMR [400 MHz, (CD3)2SO] δ 11.85 (v br s, 1 H), 8.77 (br s, 1 H), 7.44–7.37 (m, 1 H), 7.15–7.05 (m, 1 H), 7.06 (dd, J=12.5, 1.7 Hz, 1 H), 6.90 (dd, J=8.2, 1.7 Hz, 1 H), 6.81 (ddd, J=8.8, 8.8, 4.5 Hz, 1 H), 4.75 (br s, 1 H), 4.63 (t, J=5.2 Hz, 1H), 3.86 (t, J=5.0 Hz, 2 H), 3.61–3.52 (m, 4 H), 2.66 (t, J=6.9 Hz, 2 H). HRMS (EI+) calcd. for C20H16F2N2O3 370.1129 (M+), found 370.1133.

Workup

  1. customaffording a crude yellow oil after workup which
  2. filtrationwas purified by filtration through a plug of silica gel (100% EtOAc as eluant)

Sources & evidence

ORD record
ord-f15fc43c037f4f37b8ec705d194eed15
Source dataset
uspto-grants-2006_07
Patent number
US07078438B2

Reaction notes

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