4-Fluorobenzyl bromide → Methyl 3-benzyloxy-5-(4-fluorobenzyl)-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

HRID 1453862Notes

Reaction equation

HRID 1453862 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:19]([O:21][CH3:22])=[O:20])=[N:11][N:12]2[CH2:17][CH2:16][NH:15][C:14](=[O:18])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>>[CH2:1]([O:8][C:9]1[C:10]([C:19]([O:21][CH3:22])=[O:20])=[N:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:28][C:27]3[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=3)[C:14](=[O:18])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 57528498HCID 57528498, compound

Product 1

HCID 68892969Methyl 3-benzyloxy-5-(4-fluorobenzyl)-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Procedure

The title compound was prepared from methyl 3-benzyloxy-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate using a procedure similar to that found in Example 13, Step 1, except that 4-fluorobenzyl bromide was used in place of iodomethane. Purification was achieved by flash column chromatography on silica gel using a gradient elution of 0-6% MeOH/CH2Cl2, and collection and concentration of appropriate fractions afforded the title product. 1H NMR (400 MHz, CDCl3) δ 7.57-7.55 (d, 2H), 7.38-7.29 (m, 5H), 7.08-7.03 (m, 2H), 5.40 (s, 2H), 4.74 (s, 2H), 4.33-4.30 (t, 2H), 3.93 (s, 3H), 3.63-3.59 (t, 2H); ES MS (M+1)=410.

Workup

  1. customPurification
  2. washa gradient elution of 0-6% MeOH/CH2Cl2, and collection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-9fd715501f15411d8c9e146ada7cd637
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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