7-Hydrazino-quinazolin-4-ylamine → 1-(4-Amino-quinazolin-7-yl)-3-cyclopropylmethyl-6,6-dimethyl-1,5,6,7-tetrahydro-indazol-4-one

HRID 2244063Notes

Reaction equation

[NH:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH2:13])=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1)[NH2:2].[CH:14]1([CH2:17][C:18]([CH:20]2[C:25](=[O:26])[CH2:24][C:23]([CH3:28])([CH3:27])[CH2:22][C:21]2=O)=O)[CH2:16][CH2:15]1>CCO>[NH2:13][C:7]1[C:6]2[C:11](=[CH:12][C:3]([N:1]3[C:21]4[CH2:22][C:23]([CH3:28])([CH3:27])[CH2:24][C:25](=[O:26])[C:20]=4[C:18]([CH2:17][CH:14]4[CH2:16][CH2:15]4)=[N:2]3)=[CH:4][CH:5]=2)[N:10]=[CH:9][N:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

7-Hydrazino-quinazolin-4-ylamine (0.092, 16 mg) is dissolved in 1 mL EtOH and 2-(2-Cyclopropyl-acetyl)-5,5-dimethyl-cyclohexane-1,3-dione (0.092 mmol, 20.4 mg) is added. The reaction is stirred at 50° C. for 22 h. The reaction is cooled and quenched by pouring into 20 mL H2O and extracted 3 times with 5 mL CH2Cl2. The combined organics are dried with Na2SO4, concentrated, and purified by silica gel chromatography on Biotage using a gradient of 0-15% MeOH in DCM. 1-(4-Amino-quinazolin-7-yl)-3-cyclopropylmethyl-6,6-dimethyl-1,5,6,7-tetrahydro-indazol-4-one is isolated (1 mg, LC/MS m/z=362 [M+H]+)) as a white powder.

Workup

temperatureThe reaction is cooled
customquenched
additionby pouring into 20 mL H2O
extractionextracted 3 times with 5 mL CH2Cl2
dry with materialThe combined organics are dried with Na2SO4
concentrationconcentrated
custompurified by silica gel chromatography on Biotage

Sources & evidence

ORD record: ord-4f6ad5202a0343ab8a2333406002962f
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678803B2

Reaction notes

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