1H-indazol-3-amine → HCID 178499486, compound

HRID 2276327Notes

Reaction equation

HRID 2276327 reaction equation
[C:1]([CH:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([O:7]C)=O)(=O)[CH3:2].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([NH2:23])=[N:15]1>C1(C)C=CC=CC=1>[OH:7][C:5]1[N:15]2[N:14]=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]3)=[C:16]2[N:23]=[C:1]([CH3:2])[C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 133991H-indazol-3-amineHCID 112039Dimethyl acetylsuccinate

Product 1

HCID 178499486HCID 178499486, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of a dimethyl acetylsuccinate (1.55 g; 8.27 mmol) and 1H-indazol-3-amine (1 g; 7.5 mmol) in toluene (7.5 mL) was heated to reflux under a Dean Stark system for 48 h. The precipitate was filtered-off, washed with toluene and diethylether to afford 1.34 g (67%) of methyl 2-(4-hydroxy-2-methylpyrimido[1,2-b]indazol-3-yl)acetate, which was used for the next step without any further purification. ESI/APCI(+): 272 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a Dean Stark system for 48 h
  3. washwashed with toluene and diethylether

Sources & evidence

ORD record
ord-8d43f3c6c5e54e43be88fb38fcc3b212
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

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