Potassium Carbonate → N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide

HRID 2077533Notes

Reaction equation

HRID 2077533 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:9][CH:10]([CH3:12])[CH3:11])[C:5]([Cl:8])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:21]2[CH:33]=[CH:32][C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[CH:22]=2)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([C:21]2[CH:33]=[CH:32][C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[CH:22]=2)=[CH:3][C:4]=1[NH:9][CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamideHCID 575849795-bromo-2-chloro-N-(propan-2-yl)pyridin-3-amine

Product 1

HCID 57585083N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamideYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-2-chloro-N-isopropylpyridin-3-amine (127.6 mg, 0.511 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (191.5 mg, 0.602 mmol), potassium carbonate (317.8 mg, 2.299 mmol), and Pd(dppf)C12-DCM complex (42.9 mg, 0.0526 mmol) were suspended in 1,2-dimethoxyethane (2.0 ml) and water (0.5 ml). Argon was bubbled through the suspension for about 15 seconds, and then the flask was fit with a reflux condensor and placed in a preheated oil bath (100° C.) and stirred under argon for 100 minutes. The reaction was cooled to room temperature, concentrated, and treated with DCM and MeOH. These organic washings were decanted, concentrated, treated with water, and filtered. The solid was washed with water and the filtrate was discarded. Solid also washed with MeOH and Et2O, but the filtrate and solid contain product. The solid and filtrate were combined, concentrated, and purified on a silica gel column (25:1 to 20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH) to afford N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (64.5 mg, 35% yield). MS (ESI pos. ion) m/z: 361. Calculated exact mass for C17H17ClN4OS 360.

Workup

  1. customArgon was bubbled through the suspension for about 15 seconds
  2. customplaced in a preheated oil bath
  3. temperatureThe reaction was cooled to room temperature
  4. concentrationconcentrated
  5. additiontreated with DCM and MeOH
  6. customThese organic washings were decanted
  7. concentrationconcentrated
  8. additiontreated with water
  9. filtrationfiltered
  10. washThe solid was washed with water
  11. washSolid also washed with MeOH and Et2O
  12. concentrationconcentrated
  13. custompurified on a silica gel column (25:1 to 20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH)

Sources & evidence

ORD record
ord-3fa1a4119ee748d9966550b1aa1f05cc
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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