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1,2-Dimethoxyethane → 5-[2-Methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine

HRID 908393
Notes
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Reaction equation

HRID 908393 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[C:10]1[C:11]([NH2:25])=[N:12][CH:13]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:15]=1.Br[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)=[CH:29][C:28]=1[O:40][CH3:41].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:41][O:40][C:28]1[CH:29]=[C:30]([N:33]2[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]2)[CH:31]=[CH:32][C:27]=1[C:14]1[CH:15]=[C:10]([C:2]2[O:1][C:9]3[C:4]([N:3]=2)=[N:5][CH:6]=[CH:7][CH:8]=3)[C:11]([NH2:25])=[N:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 673878191-(4-Bromo-3-methoxyphenyl)-4-methylpiperazineHCID 673889723-Oxazolo[4,5-b]pyridin-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 673881955-[2-Methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine
Yield 55.1%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound [6] was prepared as follows. 3-oxazolo[4,5-b]pyridin-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (138 mg), 1-(4-bromo-3-methoxy-phenyl)-4-methyl-piperazine (97 mg), bis(triphenylphosphine) palladium (II) chloride (50.1 mg) and sodium carbonate (50.5 mg) were weighed out and sealed in a tube. DME (3 ml) and water (0.3 ml) were added. Argon was bubbled in the resulting mixture for 10 minutes then it was stirred at 100° C. for 1 hour. After cooling, the reaction mixture was diluted with ethyl acetate (5 ml), filtered, and purified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane/ethyl acetate (1/1) then 5% methanolic ammonia 7N in dichloromethane/ethyl acetate (1/1). The solvent was evaporated to dryness and the product was triturated in acetonitrile (4 ml), collected by filtration, washed with Acetonitrile and dried under vacuum at 40° C., to give 5-[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (78 mg). NMR Spectrum: (CDCl3) 2.40 (s, 3H), 2.61-2.69 (m, 4H), 3.27-3.36 (m, 4H), 3.85 (s, 3H), 6.58 (d, 1H), 6.62 (dd, 1H), 6.91 (bs, 2H), 7.25 (d, 1H), 7.30 (dd, 1H), 7.85 (dd, 1H), 8.46 (d, 1H), 8.47 (d, 1H), 8.56 (dd, 1H); Mass spectrum: M+H+ 417. There was no deprotection step.

Workup

  1. customsealed in a tube
  2. customArgon was bubbled in the resulting mixture for 10 minutes
  3. temperatureAfter cooling
  4. additionthe reaction mixture was diluted with ethyl acetate (5 ml)
  5. filtrationfiltered
  6. custompurified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane/ethyl acetate (1/1)
  7. customThe solvent was evaporated to dryness
  8. customthe product was triturated in acetonitrile (4 ml)
  9. filtrationcollected by filtration
  10. washwashed with Acetonitrile
  11. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-d85645e57dd440328183529ac49add56
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08017611B2

Reaction notes

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