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Cesium carbonate → Trifluoroacetic acid

HRID 1948068
Notes
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Reaction equation

HRID 1948068 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:32]=[CH:31][C:30](Br)=[C:29]4[C:25]=3[C:26](=[O:35])[N:27]([CH3:34])[CH2:28]4)[C:20]([C:36]([F:39])([F:38])[F:37])=[CH:19][N:18]=2)=[CH:12][CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C([O:44][C:45](=[O:53])[CH2:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)(C)(C)C.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.[C:100]([O-:103])([O-])=[O:101].[Cs+].[Cs+]>O1CCOCC1.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]>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:32]=[CH:31][C:30]([N:50]4[CH2:51][CH2:52][N:47]([CH2:46][C:45]([OH:53])=[O:44])[CH2:48][CH2:49]4)=[C:29]4[C:25]=3[C:26](=[O:35])[N:27]([CH3:34])[CH2:28]4)[C:20]([C:36]([F:38])([F:39])[F:37])=[CH:19][N:18]=2)=[CH:14][CH:15]=1)([O:5][CH2:6][CH3:7])=[O:8])[CH3:2].[F:37][C:36]([F:39])([F:38])[C:100]([OH:103])=[O:101]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2757326tert-Butyl 2-piperazinoacetateHCID 58292897Diethyl [4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate

Product 2

HCID 6422Trifluoroacetic acid
HCID 58292968
HCID 58292968, compound

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of diethyl[4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzyl]phosphonate (200.0 mg, 0.3183 mmol), piperazine-1-acetic acid tert-butyl ester (382 mg, 1.91 mmol), bis(dibenzylideneacetone)palladium (58.29 mg, 0.06366 mmol), 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (118.9 mg, 0.1910 mmol), Cs2CO3 (0.3111 g, 0.9548 mmol) in 1,4-dioxane (20 mL) was evacuated and purged with nitrogen three times. The mixture was stirred at 100° C. for 2 days. The crude mixture was purified by MDP. The purified ester was taken up in methylene chloride (1.2 mL) and trifluoroacetic acid (0.6 mL) and the mixture was stirred at room temperature for 3 hours. The crude product was purified by MDP to obtain the title compound as a trifluoroacetic acid salt. 1H NMR (400 MHz, methanol-d4) δ=1.27 (t, J=7.1 Hz, 6H), 3.19 (s, 3H), 3.29 (d, J=21.5 Hz, 2H), 3.41 (br. s., 4H), 3.60 (br. s., 4H), 4.07 (qd, J=7.2, 6.9 Hz, 4H), 4.17 (s, 2H), 4.51 (s, 2H), 7.26 (d, J=9.1 Hz, 1H), 7.34 (d, J=6.6 Hz, 2H), 7.57 (d, J=7.8 Hz, 2H), 8.36 (s, 1H), 8.69 (br. s., 1H). MS (ES+): m/z 692.27 (100) [MH+]; HPLC: tR=0.78 min (UPLC, purity).

Workup

  1. customwas evacuated
  2. custompurged with nitrogen three times
  3. customThe crude mixture was purified by MDP
  4. stirringtrifluoroacetic acid (0.6 mL) and the mixture was stirred at room temperature for 3 hours
  5. customThe crude product was purified by MDP

Sources & evidence

ORD record
ord-ca3d43f8b4fc4f3c8af4f065eb636f3a
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399433B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes