Water → HCID 117677375, compound

HRID 881986Notes

Reaction equation

HRID 881986 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=2)[C:16]([NH:18][CH:19]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH3:20])=[O:17])[CH2:10][CH2:9]1.C(NCC)C.[Cl:37][C:38]1[N:43]=[C:42](Cl)[CH:41]=[CH:40][N:39]=1.O>CC#N>[Cl:37][C:38]1[N:43]=[C:42]([N:24]2[CH2:25][CH2:26][CH:21]([CH:19]([NH:18][C:16](=[O:17])[C:15]3[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=[C:13]([O:12][CH2:11][CH:8]4[CH2:10][CH2:9]4)[CH:14]=3)[CH3:20])[CH2:22][CH2:23]2)[CH:41]=[CH:40][N:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 775312,4-DichloropyrimidineHCID 89464685HCID 89464685, compound

Product 1

HCID 117677375HCID 117677375, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(cyclopropylmethoxy)-5-methoxy-N-(1-(piperidin-4-yl)ethyl)benzamide 2,2,2-trifluoroacetate (Example 36, step ii, 2.0 g), diethyl amine (3 ml) and 2,4-dichloro-pyrimidine (550 mg) in CH3CN (80 ml) was stirred at room temperature for 30 minutes. 30 mL H2O was added and the product was extracted into ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by using normal phase chromatography eluting with petroleum ether containing 15% ethyl acetate to give N-(1-(1-(2-chloropyrimidin-4-yl)piperidin-4-yl)ethyl)-3-(cyclopropylmethoxy)-5-methoxybenzamide (740 mg) as a white solid.

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified
  6. washeluting with petroleum ether containing 15% ethyl acetate

Sources & evidence

ORD record
ord-15a7590885774455a20ba3dc2bbfaab7
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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