Acetic Anhydride → (3-(Benzo[b]thiophen-2-ylmethyl)-4-chloro-2-methoxyquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methyl acetate

HRID 926526Notes

Reaction equation

HRID 926526 reaction equation
[H-].[Na+].[S:3]1[C:7]([CH2:8][C:9]2[C:10]([O:38][CH3:39])=[N:11][C:12]3[C:17]([C:18]=2[Cl:19])=[CH:16][C:15]([C:20]([C:32]2[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=2)([C:22]2[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=2)[OH:21])=[CH:14][CH:13]=3)=[CH:6][C:5]2[CH:40]=[CH:41][CH:42]=[CH:43][C:4]1=2.[C:44](OC(=O)C)(=[O:46])[CH3:45].C([O-])(O)=O.[Na+]>CN(C=O)C>[C:44]([O:21][C:20]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([O:38][CH3:39])[C:9]([CH2:8][C:7]1[S:3][C:4]3[CH:43]=[CH:42][CH:41]=[CH:40][C:5]=3[CH:6]=1)=[C:18]2[Cl:19])([C:32]1[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=1)[C:22]1[CH:23]=[N:24][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:27]=1)(=[O:46])[CH3:45]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 74220613(3-(Benzo[b]thiophen-2-ylmethyl)-4-chloro-2-methoxyquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol2×

Product 1

HCID 118006203(3-(Benzo[b]thiophen-2-ylmethyl)-4-chloro-2-methoxyquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.12 g, 2.98 mmol) was added to a yellow solution of (3-(benzo[b]thiophen-2-ylmethyl)-4-chloro-2-methoxyquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol (0.88 g, 1.49 mmol, Intermediate 51: step c) in dry DMF (25 mL) at room temperature. The mixture was stirred at room temperature for 45 minutes and then acetic anhydride (0.28 mL, 2.98 mmol) was added. The resulting dark mixture was stirred at room temperature overnight. Ice was added followed by NaHCO3 (saturated aqueous solution). The aqueous mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to provide the title compound which was carried on to the next step without further purification.

Workup

  1. stirringThe resulting dark mixture was stirred at room temperature overnight
  2. additionIce was added
  3. extractionThe aqueous mixture was extracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-533ee156050a45b48c58d4f37eb7f6c0
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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