Sodium Acetate → HCID 178428323, compound

HRID 2046974Notes

Reaction equation

[C:1]([C:4]1[C:5](Cl)=[N:6][C:7]([NH:23][C:24]2[C:29]([O:30][CH:31]([CH3:33])[CH3:32])=[CH:28][C:27]([CH:34]3[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]3)=[C:26]([CH3:47])[CH:25]=2)=[N:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])(=O)[CH3:2].[Cl-].[Cl-].[NH2:51][NH2:52].C([O-])(=O)C.[Na+]>CCO>[CH:31]([O:30][C:29]1[CH:28]=[C:27]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[C:26]([CH3:47])=[CH:25][C:24]=1[NH:23][C:7]1[N:6]=[C:5]2[NH:51][N:52]=[C:1]([CH3:2])[C:4]2=[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:18])=[O:19])[N:8]=1)([CH3:32])[CH3:33]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl 4-(4-(5-acetyl-4-chloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-2-ylamino)-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate (81 mg, 0.12 mmol) in EtOH (2 mL) was added hydrazine dichloride (36 mg, 0.34 mmoL) and sodium acetate (47 mg, 0.57 mmol) sequentially, and the reaction mixture was heated at 80° C. overnight. The reaction was cooled to room temperature and concentrated in vacuo. The crude was dissolved in the solution of TFA (2 mL) in DCM (2 mL), and the reaction was stirred for 30 min, followed by concentration and purification by RP-HPLC to afford N6-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine. MS (ES+): 578.3 (MH+).

Workup

temperatureThe reaction was cooled to room temperature
concentrationconcentrated in vacuo
dissolutionThe crude was dissolved in the solution of TFA (2 mL) in DCM (2 mL)
concentrationfollowed by concentration and purification by RP-HPLC

Sources & evidence

ORD record: ord-53625d08c8584cac9026e13fafd081dd
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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