Water → HCID 68556599, compound

HRID 2036123Notes

Reaction equation

HRID 2036123 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.[NH:14]1[CH2:19][CH2:18][C:17]2([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21](=[O:29])[O:20]2)[CH2:16][CH2:15]1.C(N(CC)CC)C.O>CN(C)C=O>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:14]3[CH2:15][CH2:16][C:17]4([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[NH:22][C:21](=[O:29])[O:20]4)[CH2:18][CH2:19]3)=[CH:7][CH:6]=2)[O:12][N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13050639Spiro[3,1-benzoxazine-4,4'-piperidin]-2(1H)-oneHCID 167322943-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine

Product 1

HCID 68556599HCID 68556599, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

3-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine (690 mg) obtained in Example 43(2), spiro[3,1-benzoxazine-4,4′-piperidin]-2(1H)-one (1 g) and triethylamine (1.4 mL) were suspended in N,N-dimethylformamide (20 mL), and the suspension was stirred at 160° C. under irradiation of microwave for 15 min. The mixture was cooled to room temperature, water (200 mL) was added and the resulting precipitate was collected by filtration. The precipitate was recrystallized from ethanol to give the object product (550 mg, 42%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-0cd128f091d54349aef8398e02412925
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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