Acetyl chloride → HCID 86597678, compound

HRID 547769Notes

Reaction equation

HRID 547769 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[CH3:21])[C:11]([N:22]([CH3:42])[C:23](=[O:41])[C:24]([C:27]3[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=3)([CH3:26])[CH3:25])=[CH:10][N:9]=2)[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.[C:52](Cl)(=[O:54])[CH3:53]>ClCCl>[C:52]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[CH3:21])[C:11]([N:22]([CH3:42])[C:23](=[O:41])[C:24]([C:27]3[CH:28]=[C:29]([C:37]([F:39])([F:40])[F:38])[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=3)([CH3:26])[CH3:25])=[CH:10][N:9]=2)[CH2:4][CH2:3]1)(=[O:54])[CH3:53]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 86597679HCID 86597679, compound

Product 1

HCID 86597678HCID 86597678, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 80 mg (0.13 mmol) N-[4-amino-4′-(4-fluoro-2-methyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide and 26 mg (0.20 mmol) N,N-diisopropylethylamine in 3 ml dichloromethane were added 12 mg (0.15 mmol) acetyl chloride at 0° C. The reaction mixture was stirred at room temperature for 18 h. The mixture was diluted with 10 ml dichloromethane and washed with 10 ml of a saturated aqueous solution of sodium carbonate. The combined organic layers were dried over sodium sulfate, concentrated and purified by flash chromatography to give 82 mg (95%) of the title compound as a white foam.

Workup

  1. washwashed with 10 ml of a saturated aqueous solution of sodium carbonate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d93b32a7e656472eab812641644a2dbf
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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