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Azetidine → HCID 178505982, compound

HRID 1968579
Notes
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Reaction equation

HRID 1968579 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4]([NH:14][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][N:16]=2)[CH:3]=1.C([N:28]([CH2:32][CH3:33])[CH:29](C)C)(C)C.N1CCC1>C(O)CCC>[N:28]1([C:2]2[N:7]=[C:6]([CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[N:5]=[C:4]([NH:14][C:15]3[C:23]4[C:18](=[N:19][CH:20]=[C:21]([F:24])[CH:22]=4)[NH:17][N:16]=3)[CH:3]=2)[CH2:29][CH2:33][CH2:32]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 178505981HCID 178505981, compound

Product 1

HCID 178505982HCID 178505982, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture containing N-(6-chloro-2-cyclohexylpyrimidin-4-yl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine (78 mg, 0.22 mmol), N, N-diisopropylethylamine (158 μL, 0.91 mmol), azetidine (45 μL, 0.67 mmol) and n-butanol (6 mL) was heated at 125° C. for 20 min in the microwave. The reaction mixture was cooled to room temperature and the resulting solid was filtered and the solid washed with Et2O, sNH4Cl and Et2O. The resulting solid was air dried to give the title compound as a white solid (48 mg, 58%). MS (ES+) m/e=368. 1H NMR: (DMSO) 1.08-1.92 (10H, m), 2.26-2.58 (3H, m), 3.89-4.06 (4H, m), 6.50 (1H, brs), 8.32-8.62 (2H, m), 9.79 (1H, s), 13.03 (1H, s)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe resulting solid was filtered
  3. washthe solid washed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-44aed7528ce842adba75d9b623a310d6
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426425B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes