Potassium Carbonate → N-[4-({2-[(3-isopropylphenyl)amino]-1,3-benzothiazol-5-yl}oxy)pyridin-2-yl]acetamide

HRID 30803

Reaction equation

HRID 30803 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[S:12][C:13]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:14]=3[N:15]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:23]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[S:12][C:13]3[CH:19]=[CH:18][C:17]([O:20][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:23]=4)=[CH:16][C:14]=3[N:15]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22832129N-(4-Chloropyridin-2-yl)acetamideHCID 860453372-(3-Isopropylphenylamino)benzo[d]thiazol-5-ol

Product 1

HCID 59790209N-[4-({2-[(3-isopropylphenyl)amino]-1,3-benzothiazol-5-yl}oxy)pyridin-2-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture containing 2-(3-isopropylphenylamino)benzo[d]thiazol-5-ol (1 eq), N-(4-chloropyridin-2-yl)acetamide (1.4 eq), potassium bis(trimethylsilyl)amide (4 eq) and potassium carbonate (1.2 eq) in dimethylformamide was subjected to the microwave at 200° C. for 15 minutes. The reaction was then partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to give the crude product. Purification on HPLC to yield N-[4-({2-[(3-isopropylphenyl)amino]-1,3-benzothiazol-5-yl}oxy)pyridin-2-yl]acetamide. HPLC=4.87 min; MS: MH+=419.

Workup

  1. customThe reaction was then partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification on HPLC

Sources & evidence

ORD record
ord-716d0c889d634a7986a80df916a44b18
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Linked notes

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