Acetyl chloride → HCID 69710480, compound

HRID 342694Notes

Reaction equation

HRID 342694 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[NH:18][C:19]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([NH2:38])[N:33]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:48](Cl)(=[O:50])[CH3:49]>C1COCC1.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[NH:18][C:19]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([NH:38][C:48](=[O:50])[CH3:49])[N:33]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:29])[F:31])[CH:23]=3)[N:21]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 15840632HCID 15840632, compound

Product 1

HCID 69710480HCID 69710480, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 4-[5-(2-aminopyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid benzyl ester (Example 12) (0.220 g, 0.421 mmole) in THF (4 mL) under argon at 0° C. was added diisopropylethylamine (0.22 mL, 1.26 mmole) followed by acetyl chloride (0.036 mL, 0.50 mmole). The reaction was stirred at 20° C. for 1 hour, diluted with water (10 mL) and product extracted with ethyl acetate (2×50 mL). The ethyl acetate extracts were dried over anhydrous sodium sulfate, filtered, concentrated and chromatographed on silica using 5% methanol/methylene chloride to give the product (0.170 g) as an oil.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialThe ethyl acetate extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica using 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-67c90219ebbf41738299c47b62a62f27
Source dataset
uspto-grants-1999_01
Patent number
US05859041

Reaction notes

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