Benzo(d)thiazol-2-amine → HCID 59351145, compound

HRID 555891Notes

Reaction equation

HRID 555891 reaction equation
C([O-])([O-])=O.[Na+].[Na+].C1(PC2C=CC=CC=2)C=CC=CC=1.[S:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[NH2:29].Cl[C:31]1[N:36]=[CH:35][C:34]([O:37][C:38]2[C:39]([CH:44]3[CH2:49][CH2:48][N:47]([C:50](=[O:52])[CH3:51])[CH2:46][CH2:45]3)=[N:40][CH:41]=[CH:42][N:43]=2)=[CH:33][CH:32]=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].C1(C)C=CC=CC=1>[S:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[NH:29][C:31]1[N:36]=[CH:35][C:34]([O:37][C:38]2[C:39]([CH:44]3[CH2:45][CH2:46][N:47]([C:50](=[O:52])[CH3:51])[CH2:48][CH2:49]3)=[N:40][CH:41]=[CH:42][N:43]=2)=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 8706Benzo(d)thiazol-2-amineHCID 10340Sodium CarbonateHCID 70017DiphenylphosphineHCID 59351380HCID 59351380, compound

Product 1

HCID 59351145HCID 59351145, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of tris(dibenzylideneacetone)dipalladium(0) (0.021 g, 0.023 mmol), Na2CO3 (0.081 g, 0.76 mmol), 9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine (0.040 g, 0.069 mmol), benzo[d]thiazol-2-amine (0.110 g, 0.732 mmol), and 1-(4-(3-(6-chloropyridin-3-yloxy)pyrazin-2-yl)piperidin-1-yl)ethanone (0.182 g, 0.547 mmol) was added PhMe (3 mL). The reaction mixture was degassed and heated to 100° C. for 40 h. The reaction mixture was diluted with Teac and the organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 80% Teac (10% MeOH) in hexanes) gave 1-(4-(3-(6-(benzo[d]thiazol-2-ylamino)pyridin-3-yloxy)pyrazin-2-yl)piperidin-1-yl)ethanone as a white solid. MS (ESI, pos. ion) m/z: 447.2 (M+1). IC50 (uM) ++.

Workup

  1. customThe reaction mixture was degassed
  2. additionThe reaction mixture was diluted with Teac
  3. washthe organic phase was washed with water (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (10% to 80% Teac (10% MeOH) in hexanes)

Sources & evidence

ORD record
ord-ed54e3f32ec84b4ca200e2fa70919cd6
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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