Bromoacetyl bromide → HCID 59504686, compound

HRID 2400596Notes

Reaction equation

HRID 2400596 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)[N:16]=2)[CH:3]=1.C(N(CC)C(C)C)(C)C.[Br:36][CH2:37][C:38](Br)=[O:39]>ClCCl.O>[Br:36][CH2:37][C:38]([NH:24][C:23]1[CH:25]=[CH:26][C:20]([C:17]2[N:16]=[C:15]([C:4]3[CH:3]=[C:2]([CH3:1])[N:6]([CH2:7][C:8]4[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=4)[N:5]=3)[O:19][N:18]=2)=[CH:21][CH:22]=1)=[O:39]

Participants

6

Reactant 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 59504632HCID 59504632, compound

Product 1

HCID 59504686HCID 59504686, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-{5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazol-3-yl}-aniline (Step 1, 150 mg, 0.434 mmol) and N,N-diisopropylethylamine (113 μL, 0.651 mmol) in dichloromethane (5 mL) was added bromoacetyl bromide (46 μL, 0.521 mmol) dropwise at a temperature of 0° C. After 5 minutes, the reaction mixture was allowed to warm to rt. After a further 2 h, the reaction mixture was diluted with an equal volume of dichloromethane, and 20 mL water were added. After separation of the organic from the aqueous layer, the organic phase was dried over anhydrous sodium sulfate. Subsequent filtration and evaporation of the solvent yielded the title compound which was obtained in pure form after stirring with cyclohexane (195 mg, 96%): 1H NMR (400 MHz, DMSO-d6) 10.70 (s, 1H), 8.03 (d, 2H), 7.80 (d, 2H), 7.18 (d, 2H), 7.10 (d, 2H), 6.90 (s, 1H), 5.44 (s, 2H), 4.09 (s, 2H), 2.32 (s, 3H), 2.28 (s, 3H); ES-MS m/z 466/468, HPLC RT (Method F) 2.45 min.

Workup

  1. waitAfter a further 2 h
  2. additionwere added
  3. customAfter separation of the organic from the aqueous layer
  4. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  5. filtrationSubsequent filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-c38b0a6a639e43d697893299d839d1e4
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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