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Benzophenone imine → HCID 57494736, compound

HRID 861130
Notes
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Reaction equation

HRID 861130 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:22]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[N:24]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([NH:16][CH:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:35](=[NH:48])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O>[CH:17]1([NH:16][C:15]2[N:10]3[N:9]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([N:48]=[C:35]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[CH:3]=4)[C:22]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]5[CH2:31][CH2:32][CH2:33][CH2:34]5)[N:24]=4)=[C:11]3[CH:12]=[CH:13][CH:14]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 10142612HCID 10142612, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 57494736HCID 57494736, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3-bromophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (3.00 g, 5.8 mmol) in toluene (60 mL) was added benzophenone imine (3.15 g, 17.4 mmol), tris(dibenzylideneacetone)dipalladium (0.26 g, 0.3 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.54 g, 0.15 mmol) and sodium tert-butoxide (1.67 g, 17.4 mmol). The reaction was heated at reflux for 5 hours, then allowed to cool to room temperature. Water and ethyl acetate were added to the reaction mixture. The phases were separated and the organic phase was washed with brine and dried (magnesium sulfate). Filtration and concentration of the filtrate followed by purification with flash chromatography (4:6 ethyl acetate:hexanes) gave N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-{3-[(diphenylmethylene)amino]phenyl}-pyrazolo[1,5-a]pyridin-7-amine (2.61 g, 73%) as a yellow solid. 1H NMR (CDCl3): δ 7.89 (d, 1H), 7.80–7.75 (m, 3H), 7.48 (m, 1H), 7.41 (m, 2H), 7.27 (m, 5H), 7.23–7.12 (m, 4H), 7.04 (s, 1H), 6.80 (d, 1H), 6.03–5.97 (m, 3H), 4.39 (m, 1H), 4.00 (m, 1H), 2.15–2.05 (m, 4H), 1.83–1.56 (m, 12H); MS m/z 618 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 5 hours
  3. customThe phases were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationFiltration and concentration of the filtrate
  7. customfollowed by purification with flash chromatography (4:6 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-db849543c9ff46d7a5e4fa51f289f06b
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07153855B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes