Potassium Carbonate → 4-(2-(4-bromophenylamino)benzo[d]thiazol-5-yloxy)-N-methylpicolinamide

HRID 1790661

반응식

HRID 1790661 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[C:30]1[CH:35]=[CH:34][N:33]=[C:32]([C:36]([NH:38][CH3:39])=[O:37])[CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[S:10][C:11]3[CH:17]=[CH:16][C:15]([O:18][C:30]4[CH:35]=[CH:34][N:33]=[C:32]([C:36]([NH:38][CH3:39])=[O:37])[CH:31]=4)=[CH:14][C:12]=3[N:13]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 220408762-[(4-Bromophenyl)amino]benzothiazol-5-ol

생성물 1

HCID 210372454-(2-(4-bromophenylamino)benzo[d]thiazol-5-yloxy)-N-methylpicolinamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The mixture containing 2-[(4-bromophenyl)amino]benzothiazol-5-ol (1 eq), Potassiumbis(trimethylsilyl)amide (4 eq), was stirred in dimethylformamide for 30 min at room temperature. To this mixture was added (4-chloro(2-pyridyl)-N-methyl-carboxamide (1 eq) and Potassium carbonate (1.2 eq) and microwaved for 6 mins at 150° C. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated. Purification on Prep LC yielded the desired product. MS: MH+=455

후처리

  1. custommicrowaved for 6 mins at 150° C
  2. concentrationThe reaction mixture was then concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification on Prep LC

출처 및 근거

ORD 기록
ord-da96264e0f81436bab3b63be0e66a636
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071216B2

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