4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 10150525, compound

HRID 1835661Notes

Reaction equation

HRID 1835661 reaction equation
[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH3:22])=[O:20])=[CH:15][C:14]=2[F:23])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.[NH2:24][O:25][CH2:26][CH2:27][OH:28].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>>[F:23][C:14]1[CH:15]=[C:16]([C:19]([NH:21][CH3:22])=[O:20])[CH:17]=[CH:18][C:13]=1[NH:12][C:3]1[C:2]([F:1])=[C:10]([F:11])[CH:9]=[CH:8][C:4]=1[C:5]([NH:24][O:25][CH2:26][CH2:27][OH:28])=[O:7]

Participants

4

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 3014186Ethanol, 2-(aminooxy)-HCID 12135111HCID 12135111, compound

Product 1

HCID 10150525HCID 10150525, compoundYield 45%

Procedure

The title compound was prepared from reaction of 3,4-difluoro-2-{2-fluoro-4-[(methylamino)carbonyl]anilino}benzoic acid with 2-(aminooxy)ethanol and DMT-MM by the general procedure of Example 3, Step B, then purified by column chromatography on silica gel (10% MeOH/CH2Cl2 as eluant) to give 2-{2-fluoro-4-[(methylamino)carbonyl]anilino}-3,4-difluoro-N-(2-hydroxyethoxy)benzamide as a crystalline cream solid (45%); m.p. (acetone) 197-200° C. 1H NMR [400 MHz, (CD3)2SO] δ 11.84 (br s, 1 H), 8.86 (br s, 1 H), 8.31 (br q, J=4.3 Hz, 1 H), 7.65 (dd, J=12.6, 1.8 Hz, 1 H), 7.55 (dd, J=8.4, 1.8 Hz, 1 H), 7.47-7.41 (m, 1 H), 7.27 (dd, J=16.9, 9.5 Hz, 1 H), 6.84 (ddd, J=8.6, 8.6, 4.8 Hz, 1 H), 4.72 (v br s, 1 H), 3.84 (t, J=4.8 Hz, 2 H), 3.56 (t, J=4.8 Hz, 2 H), 2.76 (d, J=4.5 Hz, 3 H). Anal. calcd. for C17H16F3N3O4: C, 53.3; H, 4.2; N, 11.0. Await Found.

Workup

  1. custompurified by column chromatography on silica gel (10% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-df278045989e4a248959dcd43511badc
Source dataset
uspto-grants-2004_08
Patent number
US06770778B2

Reaction notes

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