Water → HCID 11461905, compound

HRID 1670778Notes

Reaction equation

HRID 1670778 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](C(N=[N+]=[N-])=O)=[N:2]1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.O.C[N:30](C)[CH:31]=[O:32]>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([NH:30][C:31]([N:25]2[CH2:26][CH2:27][N:22]([C:19]3[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=3)[CH2:23][CH2:24]2)=[O:32])=[N:2]1

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 752601-(4-Fluorophenyl)piperazineHCID 12262769HCID 12262769, compound

Product 1

HCID 11461905HCID 11461905, compoundYield 18%

Conditions

Temperature
100 °C

Procedure

1H-Indazole-3-carbonylazide (synthesized according to the method described in Tetrahedron, 32, 4, 1976, 493-497, 200 mg) was dissolved in dimethylformamide (4 ml), and the mixture was stirred with heating at 100° C. for 30 min. 1-(4-Fluorophenyl)piperazine (Aldrich Co., 211 mg) was dissolved in dimethylformamide (1 ml) and added thereto, and the mixture was stirred with heating at 100° C. for 1 hr. After allowing to cool, water was added to the reaction mixture and the precipitated solid was collected by filtration and dried. The solid was washed in a suspension state with methanol to give 4-(4-fluorophenyl)-1-piperazinecarboxylic acid (1H-indazol-3-yl)amide (64 mg, yield 18%).

Workup

  1. additionadded
  2. stirringthe mixture was stirred
  3. temperaturewith heating at 100° C. for 1 hr
  4. temperatureto cool
  5. filtrationthe precipitated solid was collected by filtration
  6. customdried
  7. washThe solid was washed in a suspension state with methanol

Sources & evidence

ORD record
ord-e0aad95b2982452a93ff04782a8fc4f1
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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