Triethylamine → HCID 66589115, compound

HRID 1093206Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[N:5]=[C:4]2[N:17]([CH2:20][C:21]([F:24])([F:23])[F:22])[N:18]=[CH:19][C:3]=12.FC(F)(F)C(O)=O.[C@@H:32]12[CH2:38][C@@H:35]([NH:36][CH2:37]1)[CH2:34][O:33]2.C(N(CC)CC)C>C(O)C>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[C:4]3[N:17]([CH2:20][C:21]([F:24])([F:23])[F:22])[N:18]=[CH:19][C:3]3=[C:2]([N:36]3[CH2:37][C@H:32]4[CH2:38][C@@H:35]3[CH2:34][O:33]4)[N:7]=2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

Participants

Conditions

Temperature: 140 °C

Procedure

To a Smith process vial containing a suspension of 4-chloro-6-(4-nitro-phenyl)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazolo[3,4-d]pyrimidine (0.68 g, 1.9 mmol) and (1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane trifluoroacetate (prepared starting from cis-1-Boc-4-hydroxy-D-prolinate, 3.1 mmol) in ethanol (14 mL) was added triethylamine (4 mL, 31 mmol). The mixture was heated in the microwave reactor for 10 minutes at 140° C. The precipitate was collected by Buchner filtration and washed successively with methanol, water, methanol, and diethyl ether. Solid was dried under house vacuum to provide (1R,4R)-5-(6-(4-nitrophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-2-oxa-5-azabicyclo[2.2.1]heptane as a pale yellow solid (0.56 g, 70%). MS (ES+): 421.1 (M+H)+

Workup

additionTo a Smith process vial containing
filtrationThe precipitate was collected by Buchner filtration
washwashed successively with methanol, water, methanol, and diethyl ether
customSolid was dried under house vacuum

Sources & evidence

ORD record: ord-14e57c7d91d342d0aa11c8db04c86a48
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129371B2

Reaction notes

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