4-(Bromomethyl)benzoic acid → 5-Bromo-3-(5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1959420Notes

Reaction equation

HRID 1959420 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][NH2:12])=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[Br:13][CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=O)=[CH:17][CH:16]=1.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(C(C)C)C(C)C>CC#N>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[O:10][C:19]([C:18]3[CH:22]=[CH:23][C:15]([CH2:14][Br:13])=[CH:16][CH:17]=3)=[N:12][N:11]=2)[C:2]([NH2:1])=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 225994-(Bromomethyl)benzoic acidHCID 70579Triphenylphosphine dibromideHCID 81531DiisopropylethylamineHCID 580702563-Amino-6-bromopyrazine-2-carbohydrazide

Product 1

HCID 580704675-Bromo-3-(5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amineYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 3-amino-6-bromo-pyrazine-2-carbohydrazide (200 mg, 0.86 mmol) and 4-(bromomethyl)benzoic acid (185 mg, 0.86 mmol) in MeCN (4 mL) at room temperature was added dibromo(triphenyl)phosphorane (1.7 g, 4.14 mmol) and the resulting reaction mixture was stirred for 1 h. The reaction mixture was diluted with acetonitrile (2 mL) and DIPEA (668 mg, 900 μL, 5.2 mmol) was added dropwise and the suspension was allowed to stir overnight. The suspension was filtered, washed with CH3CN and hexane, and air dried to provide 5-bromo-3-(5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (240 mg, 68%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.45 (s, 1H), 8.11 (d, J=8.1 Hz, 2H), 7.72 (d, J=8.2 Hz, 2H), 4.82 (s, 2H). LC/MS m/z 412.1 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. additionwas added dropwise
  3. stirringto stir overnight
  4. filtrationThe suspension was filtered
  5. washwashed with CH3CN and hexane, and air
  6. customdried

Sources & evidence

ORD record
ord-7dbb65f850104a4fb3eb2cc391c7fe01
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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