5-(4-(Bromomethyl)phenyl)isoxazole → HCID 11989874, compound

HRID 2224263Notes

Reaction equation

HRID 2224263 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:36][N:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1>>[O:36]1[C:32]([C:29]2[CH:30]=[CH:31][C:26]([CH2:25][N:15]3[C:14](=[O:17])[N:11]4[N:12]=[CH:13][C:8]([C:5]5[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=5)=[C:9]([C:18]5[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=5)[C:10]4=[N:16]3)=[CH:27][CH:28]=2)=[CH:33][CH:34]=[N:35]1

Participants

3

Reactant 2

HCID 229975455-(4-(Bromomethyl)phenyl)isoxazoleHCID 59716620HCID 59716620, compound

Product 1

HCID 11989874HCID 11989874, compound

Procedure

The title compound was prepared by reacting 7-(4-fluorophenyl)-8-(pyridine-4-yl)-[1,2,4]-triazolo[4,3-b]pyridazin-3(2H)-one, prepared as described in Example 279F, 5-(4-(bromomethyl)phenyl)isoxazole, prepared as described in Example 250A by procedures analogous to those described in Example 2 as a yellow solid (68%). HPLC: 99% at 5.46 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O—10% MeOH—0.1% H3PO4 and B=10% H2O—90% MeOH—0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 465 [M+H]+; 1H NMR (CDCl3, 400 MHz): δ 5.25 (s, 2H), 6.51 (d, J=0.96 Hz, 1H), 7.01-7.09 (m, 2H), 7.11-7.18 (m, 2H), 7.23 (dd, J1=4.40 Hz, J2=1.76 Hz, 2H), 7.51 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.3 Hz, 2H), 8.21 (s, 1H), 8.28 (d, J=1.76 Hz, 1H), 8.61-8.64 (m, 2H).

Workup

  1. customprepared
  2. customprepared
  3. washEluted with 0% to 100% B, 8 min gradient

Sources & evidence

ORD record
ord-0352d9c8bbd94f59903a098a217b0fdf
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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