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

HRID 30803

반응식

HRID 30803 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-716d0c889d634a7986a80df916a44b18
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423150B2

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