Hydrazine → HCID 178495785, compound

HRID 2046988Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[C:6]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([CH:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])[N:5]=[C:4]([NH:29][C:30]2[CH:35]=[C:34]([CH3:36])[C:33]([CH:37]3[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][O:45][CH3:46])[CH2:39][CH2:38]3)=[CH:32][C:31]=2[O:47][CH:48]([CH3:50])[CH3:49])[N:3]=1.[NH2:51][NH2:52]>C1COCC1>[CH:48]([O:47][C:31]1[CH:32]=[C:33]([CH:37]2[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][O:45][CH3:46])[CH2:39][CH2:38]2)[C:34]([CH3:36])=[CH:35][C:30]=1[NH:29][C:4]1[N:3]=[C:2]2[NH:51][N:52]=[C:8]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:7]2=[C:6]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:25])[N:5]=1)([CH3:50])[CH3:49]

Participants

Conditions

Temperature: 120 °C

Procedure

To a 10 mL microwave reaction tube was added (4-chloro-2-(2-isopropoxy-4-(1-(2-methoxyethyl)piperidin-4-yl)-5-methylphenylamino)-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanone (0.0548 mmol), THF (4 mL) and H2NNH2 (0.4 mL). The resulting mixture was stirred at 120° C. for 30 minutes by using a microwave machine. The reaction solution was concentrated in vacuo and the residue was purified by reverse phase HPLC to afford N6-(2-isopropoxy-4-(1-(2-methoxyethyl)piperidin-4-yl)-5-methylphenyl)-N4-(2-(isopropylsulfonyl)phenyl)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine as a slightly yellow solid. MS (ES+): 698.30 (MH+).

Workup

concentrationThe reaction solution was concentrated in vacuo
customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-2da090d19a7d46df88a8a2c4eecca806
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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