Sodium Carbonate → HCID 89689588, compound

HRID 595398Notes

Reaction equation

HRID 595398 reaction equation
Cl[C:2]1[CH:9]=[C:8]([NH:10][CH:11]([CH3:13])[CH3:12])[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:23]=[CH:22][C:18]2[N:19]=[CH:20][S:21][C:17]=2[CH:16]=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:21]1[C:17]2[CH:16]=[C:15]([NH:14][C:2]3[CH:9]=[C:8]([NH:10][CH:11]([CH3:13])[CH3:12])[C:5]([C:6]#[N:7])=[CH:4][N:3]=3)[CH:23]=[CH:22][C:18]=2[N:19]=[CH:20]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 89689825HCID 89689825, compound

Product 1

HCID 89689588HCID 89689588, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
115 °C

Procedure

To a solution of 6-chloro-4-(isopropylamino)nicotinonitrile (18) (1 g, 5.1 mmol) in dioxane (40 mL): H2O (4 mL), 6-amino benzothiazole (5.1 mmol, 1 equiv.), xanthphos (2.0 mmol, 0.4 equiv.) and Na2CO3 (20.5 mmol, 4 equiv.) were added and degassed for 10 min. To the reaction mixture Pd2(dba)3 (2.0 mmol, 0.4 equiv.) was added and degassed again for 10 min. It was then heated at 115° C. for overnight. The reaction mixture was cooled and filtered through small pad of celite. The filtrate obtained was concentrated and the crude material was purified by column chromatography through silica gel and MeOH: CHCl3 as eluent to afford 6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinonitrile.

Workup

  1. customdegassed for 10 min
  2. customdegassed again for 10 min
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through small pad of celite
  5. customThe filtrate obtained
  6. concentrationwas concentrated
  7. customthe crude material was purified by column chromatography through silica gel and MeOH

Sources & evidence

ORD record
ord-6151318597c54d5e91449dc382fecf99
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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