Triethylamine → HCID 66588996, compound

HRID 1093202Notes

Reaction equation

HRID 1093202 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.Cl.[C@H:26]12[CH2:32][C@H:29]([NH:30][CH2:31]1)[CH2:28][O:27]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:30]3[CH2:31][C@@H:26]4[CH2:32][C@H:29]3[CH2:28][O:27]4)[N:7]=2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 576542484-Chloro-6-(4-nitrophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-D]pyrimidine

Product 1

HCID 66588996HCID 66588996, compoundYield 118.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °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 (0.30 g, 0.84 mmol) and (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride (0.12 g, 0.88 mmol) in ethanol (4 mL) was added triethylamine (0.33 mL, 2.5 mmol). The mixture was heated in the microwave reactor for 15 minutes at 120° C. The precipitate was collected by Buchner filtration, washed with methanol, and dried under house vacuum to provide (1S,4S)-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 bright yellow powder (0.42 g, >100%). MS (ES+): 421.1 (M+H)+

Workup

  1. additionTo a Smith process vial containing
  2. filtrationThe precipitate was collected by Buchner filtration
  3. washwashed with methanol
  4. customdried under house vacuum

Sources & evidence

ORD record
ord-80f7fe34e50446fe84aad9b2e3006ffe
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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