Hydrochloric Acid → 5-(Piperidin-4-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047114Notes

Reaction equation

C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)[CH:9]=1.C(O)C.O.Cl>O1CCOCC1.C(Cl)Cl>[NH:30]1[CH2:31][CH2:32][CH:27]([C:10]2[CH:9]=[C:8]([NH2:7])[N:13]3[N:14]=[CH:15][C:16]([C:17]4[CH:18]=[N:19][C:20]5[C:25]([CH:26]=4)=[CH:24][CH:23]=[CH:22][CH:21]=5)=[C:12]3[N:11]=2)[CH2:28][CH2:29]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a 20 mL scintillation vial was charged tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)-amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (80 μmol, 56 mg) followed by ethanol (2 mL) and H2O (500 μL). To this solution was added 2 mL of 4N HCl in 1,4-dioxane. This solution was heated to 60° C. for 2 hours. Upon completion, the reaction mixture was diluted with DCM (10 mL) and washed with NaHCO3(aq) and extracted with DCM twice more. The combined organics were then dried over Na2SO4 and the solvent was removed in vacuo to yield 5-(piperidin-4-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (20.3 mg, 59 umol) as cream-colored solid

Workup

washwashed with NaHCO3(aq)
extractionextracted with DCM twice more
dry with materialThe combined organics were then dried over Na2SO4
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-795558556ec54a31a4acb3bdba84d75e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

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