5-Hydroxymethylene-1-methyl-1,3a,5,6,7,7a-hexahydro-indazol-4-one → 3-(7-Methyl-5,7-dihydro-6H-pyrazolo[3,4-h]quinazolin-2-ylamino)-phenol

HRID 643757

Reaction equation

HRID 643757 reaction equation
O[CH:2]=[C:3]1[CH2:11][CH2:10][CH:9]2[CH:5]([CH:6]=[N:7][N:8]2[CH3:12])[C:4]1=O.[OH:14][C:15]1[CH:16]=[C:17]([NH:21][C:22]([NH2:24])=[NH:23])[CH:18]=[CH:19][CH:20]=1>CN(C=O)C>[CH3:12][N:8]1[C:9]2[CH2:10][CH2:11][C:3]3[CH:2]=[N:23][C:22]([NH:21][C:17]4[CH:16]=[C:15]([OH:14])[CH:20]=[CH:19][CH:18]=4)=[N:24][C:4]=3[C:5]=2[CH:6]=[N:7]1

Participants

4

Reactant 2

HCID 674058435-Hydroxymethylene-1-methyl-1,3a,5,6,7,7a-hexahydro-indazol-4-oneHCID 178418735HCID 178418735, compound

Product 1

HCID 113238313-(7-Methyl-5,7-dihydro-6H-pyrazolo[3,4-h]quinazolin-2-ylamino)-phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To the DMF solution of crude 5-hydroxymethylene-1-methyl-1,3a,5,6,7,7a-hexahydro-indazol-4-one was added 10 eq of N-(3-hydroxy-phenyl)-guanidine, the reaction mixture was stirred at 100° C. for overnight, LC/MS indicated one of the two peaks is the desired product. The DMF solution of reaction mixture was directly injected into prep HPLC, only a portion of the product mixture was purified.

Sources & evidence

ORD record
ord-5e1460234b744c78af242c55d5888b8f
Source dataset
uspto-grants-2010_04
Patent number
US07700609B2

Linked notes

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