4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 22025626, compound

HRID 2181452Notes

Reaction equation

HRID 2181452 reaction equation
[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][C:14]=2[F:23])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].[NH2:24][O:25][CH2:26][CH2:27][O:28][CH:29]=[CH2:30].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>>[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][OH:22])=[CH:15][C:14]=2[F:23])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([O:7][CH3:26])=[O:6].[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][C:14]=2[F:23])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([NH:24][O:25][CH2:26][CH2:27][O:28][CH:29]=[CH2:30])=[O:7]

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 22025707HCID 22025707, compound

Product 2

HCID 22025626HCID 22025626, compoundYield 46%HCID 22025700HCID 22025700, compound

Procedure

The title compound was prepared from reaction of 3,4-difluoro-2-[2-fluoro-4-(3-hydroxypropyl)anilino]benzoic acid with 1-[2-(aminooxy)ethoxy]ethylene and DMT-MM by the general procedure of Example 6, Step B, then purified by column chromatography on silica gel (20% EtOAc/PE as eluant) to give 3,4-difluoro-2-[2-fluoro-4-(3-hydroxypropyl)anilino]-N-[2-(vinyloxy)ethoxy]benzamide as a white solid (46%), which was employed directly in the next step. 1H NMR [400 MHz, (CD3)2SO] δ 11.93 (br s, 1 H), 8.79 (br s, 1 H), 7.44-7.38 (m, 1 H), 7.14-7.05 (m, 1 H), 7.04 (dd, J=12.6, 1.6 Hz, 1 H), 6.89 (dd, J=8.2, 1.6 Hz, 1 H), 6.82 (ddd, J=8.7, 8.7, 4.4 Hz, 1 H), 6.50 (dd, J=14.3, 6.7 Hz, 1 H), 4.45 (t, J=5.1 Hz, 1 H), 4.18 (dd, J=14.3, 1.9 Hz, 1 H), 4.06-4.01 (m, 2 H), 3.98 (dd, J=6.6, 1.9 Hz, 1 H), 3.89-3.82 (m, 2 H), 3.42-3.35 (m, 2 H), 2.56 (t, J=7.7 Hz, 2 H), 1.72-1.64 (m, 2 H). LCMS (APCI−) 409 (M−H).

Workup

  1. custompurified by column chromatography on silica gel (20% EtOAc/PE as eluant)

Sources & evidence

ORD record
ord-8a0824a0095f43499a570a02d8c59c71
Source dataset
uspto-grants-2005_05
Patent number
US06891066B2

Reaction notes

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