Indole-3-Acetic Acid → HCID 135554950, compound

HRID 1379029Notes

Reaction equation

HRID 1379029 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=O)=[CH:2]1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[F:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[C:50]([C:51]3[CH:56]=[CH:55][N:54]=[CH:53][CH:52]=3)=[C:45]3[NH:46][NH:47][CH2:48][CH2:49][N:44]3[N:43]=2)=[CH:38][CH:37]=1>CN(C)C=O.O>[F:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[C:50]([C:51]3[CH:56]=[CH:55][N:54]=[CH:53][CH:52]=3)=[C:45]3[NH:46][N:47]([C:11](=[O:13])[CH2:10][C:3]4[C:4]5[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=5)[NH:1][CH:2]=4)[CH2:48][CH2:49][N:44]3[N:43]=2)=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 802Indole-3-Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 135554955HCID 135554955, compound

Product 1

HCID 135554950HCID 135554950, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3-indolylacetic acid (57 mg, 0.325 mmol), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide (50 mg, 0.325 mmol) and 1-hydroxybenzotriazole (44 mg, 0.325 mmol) in N,N-dimethylformamide (0.6 ml) was stirred for 1 hour at ambient temperature. Then to the mixture was added 7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (80 mg, 0.271 mmol) in N,N-dimethylformamide (1 ml). After stirring for 2 hours, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by crystallization from ethyl acetate to give 7-(4-fluorophenyl)-2-(3-indolylacetyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (87 mg).

Workup

  1. stirringAfter stirring for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-6ef2de47e00c4f9da473989b9d017422
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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