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

HRID 13444

Reaction equation

HRID 13444 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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-methylcarboxamide (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

Workup

  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

Sources & evidence

ORD record
ord-b74b775937df4e8fb60155f9f1e1da68
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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