Sodium Carbonate → HCID 89690920, compound

HRID 595443Notes

Reaction equation

HRID 595443 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])[C:5]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:32]=[CH:31][C:27]2[N:28]=[CH:29][S:30][C:26]=2[CH:25]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Na+].[Na+]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[S:30]1[C:26]2[CH:25]=[C:24]([NH:23][C:2]3[CH:7]=[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])[C:5]([C:12]4[O:13][C:14]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)=[N:15][N:16]=4)=[CH:4][N:3]=3)[CH:32]=[CH:31][C:27]=2[N:28]=[CH:29]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 682886-AminobenzothiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 89689517HCID 89689517, compound

Product 1

HCID 89690920HCID 89690920, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To solution of 2-chloro-N-isopropyl-5-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-4-amine (200 mg, 0.6 mmol) in dioxane (10 mL): H2O (2 mL), 6-amino benzothiazole (0.63 mmol, 1 equiv.), xanthphos (0.2 mmol, 0.4 equiv.) and Na2CO3 (2.5 mmol, 4 equiv.) were added and degassed for 10 min. To the reaction mixture Pd2(dba)3 (0.2 mmol, 0.4 equiv.) was added and degassed again for 10 min. It was then heated at 110° C. for overnight. The reaction mass was cooled and filtered through small pad of celite. The filtrate obtained was concentrated to provide crude material. The crude material was purified by column chromatography through silica gel and MeOH: DCM as eluent. The material obtained was further purified by prep. HPLC to afford N2-(benzo[d]thiazol-6-yl)-N4-isopropyl-5-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine-2,4-diamine

Workup

  1. customdegassed for 10 min
  2. customdegassed again for 10 min
  3. temperatureThe reaction mass was cooled
  4. filtrationfiltered through small pad of celite
  5. customThe filtrate obtained
  6. concentrationwas concentrated
  7. customto provide crude material
  8. customThe crude material was purified by column chromatography through silica gel and MeOH
  9. customThe material obtained
  10. customwas further purified by prep

Sources & evidence

ORD record
ord-8d7c0677ef0149d89e249c600111a983
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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