Potassium Carbonate → HCID 67347521, compound

HRID 1970177Notes

Reaction equation

HRID 1970177 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[C:17]4[S:21][C:20]([N:22]([C@H:24]5[CH2:29][CH2:28][NH:27][CH2:26][C@H:25]5[F:30])[CH3:23])=[N:19][C:18]4=[O:31])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:34]([F:37])([F:36])[F:35])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:45][C:46]([NH2:48])=[O:47]>CN(C=O)C>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[C:17]4[S:21][C:20]([N:22]([CH3:23])[C@H:24]5[CH2:29][CH2:28][N:27]([CH2:45][C:46]([NH2:48])=[O:47])[CH2:26][C@H:25]5[F:30])=[N:19][C:18]4=[O:31])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:34]([F:36])([F:37])[F:35])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 67347499HCID 67347499, compound

Product 1

HCID 67347521HCID 67347521, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-({1-[4-Chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2-{[(3R,4S)-3-fluoropiperidin-4-yl](methyl)amino}-1,3-thiazol-4(5H)-one (previous Example 54) (90 mg, 0.16 mmol) in DMF (2 mL) was added potassium carbonate (45 mg, 0.32 mmol) followed by 2-Bromo-acetamide (27 mg, 0.20 mmol). The reaction mixture was stirred at room temperature for 4 hours and partitioned between water and ethyl acetate. The ethyl acetate layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (5% methanol in dichloromethane) to yield the title compound (63 mg, 64%).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude solid
  7. customThe crude solid was purified via flash chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7314ac06f8b04f8b8fce1ac0bf25f143
Source dataset
uspto-grants-2013_04
Patent number
US08426604B2

Reaction notes

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