Potassium Carbonate → N-[4-({2-[(3-tert-butylphenyl)amino]-1,3-benzothiazol-5-yl}oxy)pyridin-2-yl]-1-methylpiperidine-4-carboxamide

HRID 30806

Reaction equation

HRID 30806 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:15]=3[N:16]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(=O)([O-])[O-].[K+].[K+].Cl[C:39]1[CH:44]=[CH:43][N:42]=[C:41]([NH:45][C:46]([CH:48]2[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]2)=[O:47])[CH:40]=1>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([O:21][C:39]4[CH:44]=[CH:43][N:42]=[C:41]([NH:45][C:46]([CH:48]5[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]5)=[O:47])[CH:40]=4)=[CH:17][C:15]=3[N:16]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 69008397N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamideHCID 860453232-(3-Tert-butylphenylamino)benzo[d]thiazol-5-ol

Product 1

HCID 59790078N-[4-({2-[(3-tert-butylphenyl)amino]-1,3-benzothiazol-5-yl}oxy)pyridin-2-yl]-1-methylpiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture containing 2-(3-tert-butylphenylamino)benzo[d]thiazol-5-ol (1 eq), potassium bis(trimethylsilyl)amide (4 eq), and potassium carbonate (1.2 eq) in dimethylformamide was stirred at room temperature for 10 minutes. N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide (1.4 eq) was then added and mixture subjected to microwave at 220° C. for 20 minutes. Reaction partitioned between ethyl acetate and water. Organic layer separated, washed with brine, dried over sodium sulfate and concentrated to give crude product. Purification by HPLC to yield N-[4-({2-[(3-tert-butylphenyl)amino]-1,3-benzothiazol-5-yl}oxy)pyridin-2-yl]-1-methylpiperidine-4-carboxamide. HPLC=4.74 min; MS: MH+=516.

Workup

  1. waitto microwave at 220° C. for 20 minutes
  2. customReaction
  3. custompartitioned between ethyl acetate and water
  4. customOrganic layer separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give crude product
  9. customPurification by HPLC

Sources & evidence

ORD record
ord-4adb3169209d4cafaefd829c100a5310
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Linked notes

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