4-(Bromomethyl)benzoic acid → 1-[4-[5-Amino-6-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-1-piperidyl]propan-1-one

HRID 1959479Notes

Reaction equation

HRID 1959479 reaction equation
BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:22][C:23]1[C:24]([C:39]([NH:41][NH2:42])=[O:40])=[N:25][C:26]([CH:29]2[CH2:34][CH2:33][N:32]([C:35](=[O:38])[CH2:36][CH3:37])[CH2:31][CH2:30]2)=[CH:27][N:28]=1.[Br:43][CH2:44][C:45]1[CH:53]=[CH:52][C:48]([C:49](O)=O)=[CH:47][CH:46]=1.CCN(C(C)C)C(C)C>CC#N.C(OCC)(=O)C>[NH2:22][C:23]1[N:28]=[CH:27][C:26]([CH:29]2[CH2:30][CH2:31][N:32]([C:35](=[O:38])[CH2:36][CH3:37])[CH2:33][CH2:34]2)=[N:25][C:24]=1[C:39]1[O:40][C:49]([C:48]2[CH:52]=[CH:53][C:45]([CH2:44][Br:43])=[CH:46][CH:47]=2)=[N:42][N:41]=1

Participants

7

Reactant 4

HCID 225994-(Bromomethyl)benzoic acidHCID 70579Triphenylphosphine dibromideHCID 81531DiisopropylethylamineHCID 667444223-Amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carbohydrazide

Product 1

HCID 667445751-[4-[5-Amino-6-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-1-piperidyl]propan-1-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dibromo(triphenyl)phosphorane (682 mg, 1.6 mmol) was added to a suspension of 3-amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carbohydrazide (105 mg, 0.36 mmol) and 4-(bromomethyl)benzoic acid (77 mg, 0.36 mmol) in MeCN (2 mL) at room temperature and the resulting solution was stirred for 1 h under an atmosphere of nitrogen. DIPEA (278.5 mg, 375.3 μL, 2.155 mmol) was added dropwise and the solution was stirred for 2 h. The reaction mixture was diluted with ethyl acetate, washed with 50% saturated sodium bicarbonate solution (2×20 mL), water, and brine. The solution was dried over anhydrous Na2SO4, filtered, concentrated in vacuo to obtain 1-[4-[5-amino-6-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-1-piperidyl]propan-1-one, which was taken to the next step without further purification.

Workup

  1. stirringthe solution was stirred for 2 h
  2. washwashed with 50% saturated sodium bicarbonate solution (2×20 mL), water, and brine
  3. dry with materialThe solution was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd9498a7f58a48bfa9a767406afa3fb0
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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