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Trifluoroacetic acid → HCID 57813540, compound

HRID 564640
Notes
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Reaction equation

HRID 564640 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[CH2:22]([N:24]1[C:28]2=[N:29][C:30]([CH2:69][CH3:70])=[C:31]([CH2:40][NH:41][C:42]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([NH:52][CH2:53][C:54]4[CH:59]=[CH:58][CH:57]=[C:56](B5OC(C)(C)C(C)(C)O5)[CH:55]=4)=[O:51])[CH:45]=3)=[O:43])[C:32]([NH:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:27]2[CH:26]=[N:25]1)[CH3:23].C([O-])([O-])=O.[K+].[K+].C(O)(C(F)(F)F)=O>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH2:22]([N:24]1[C:28]2=[N:29][C:30]([CH2:69][CH3:70])=[C:31]([CH2:40][NH:41][C:42]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([NH:52][CH2:53][C:54]4[CH:59]=[C:58]([C:2]5[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:9]6[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]6)[CH:3]=5)[CH:57]=[CH:56][CH:55]=4)=[O:51])[CH:45]=3)=[O:43])[C:32]([NH:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:27]2[CH:26]=[N:25]1)[CH3:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 224929571-Boc-4-(3-bromophenoxy)piperidineHCID 57813501HCID 57813501, compound

Product 1

HCID 57813540HCID 57813540, compoundYield 33.1%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 1,1-dimethylethyl 4-[(3-bromophenyl)oxy]-1-piperidinecarboxylate (0.036 g, 0.100 mmol) in 1,4-dioxane (0.9 mL) and H2O (300 μL) was added N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-1,3-benzenedicarboxamide (0.067 g, 0.1 mmol), Pd(Ph3P)4 (4.62 mg, 4.00 μmol), and K2CO3 (0.028 g, 0.200 mmol). This mixture was heated at 130° C. for 15 min. The reaction mixture was concentrated (Glas-Col) and purified with CombiFlash chromatograph. To the resultant material was added DCM (300 μL) and TFA (100 μL, 1.298 mmol) which was then stirred at room temperature for 30 min. The reaction mixture was concentrated (Glas-Col), purified using a Gilson HPLC (with 0.1% TFA), concentrated on a GeneVac EZ-2 and neutralized with an amine cartridge to afford 0.0237 g (33.1%) of the title compound. LC-MS m/z 716 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 1.39 (t, J=6.78 Hz, 3 H) 1.48 (t, J=6.90 Hz, 3 H) 1.80-1.97 (m, 2 H) 1.99-2.24 (m, 5 H) 3.09-3.28 (m, 4 H) 3.41 (t, J=9.29 Hz, 2 H) 3.66 (t, J=11.04 Hz, 2 H) 4.02 (d, J=8.78 Hz, 2 H) 4.33 (br. s., 1 H) 4.42-4.90 (m, 8 H) 6.61-6.85 (m, 1 H) 6.94-7.17 (m, 1 H) 7.21 (br. s, 2 H) 7.31-7.66 (m, 5 H) 8.04 (d, J=7.53 Hz, 2 H) 8.27 (br. s., 1 H) 8.35-8.44 (m, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated (Glas-Col)
  2. custompurified with CombiFlash chromatograph
  3. concentrationThe reaction mixture was concentrated (Glas-Col)
  4. custompurified
  5. concentrationconcentrated on a GeneVac EZ-2

Sources & evidence

ORD record
ord-433c4d99b9554dd5928bf4c2a11d7ede
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08067408B2

Reaction notes

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