Acetic Acid → HCID 178494789, compound

HRID 2207120Notes

Reaction equation

HRID 2207120 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([CH2:11][CH2:12][O:13][CH3:14])[CH:8]=[C:7]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]([O:25][C:26](=[O:37])[NH:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([CH2:34][CH:35]=O)[CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22].CC(O)=O.[Na]>ClCCCl.O>[C:21]([O:25][C:26](=[O:37])[NH:27][C@H:28]1[CH2:29][CH2:30][C@H:31]([CH2:34][CH2:35][N:18]2[CH2:17][CH2:16][N:15]([C:7]3[CH:8]=[C:9]([CH2:11][CH2:12][O:13][CH3:14])[N:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[N:6]=3)[CH2:20][CH2:19]2)[CH2:32][CH2:33]1)([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5360545SodiumHCID 86725454HCID 86725454, compoundHCID 178453924HCID 178453924, compound

Product 1

HCID 178494789HCID 178494789, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A mixture of 2-tert-butyl-4-(2-methoxy-ethyl)-6-piperazin-1-yl-pyrimidine (500 mg, 1.796 mmol), trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (433 mg, 1.796 mmol) and AcOH (108 mg, 1.796 mmol) in DCE (30 ml) was stirred at room temperature for 10 min. Sodium triacetoxyhydroborate (571 mg, 2.69 mmol) was added. After 4 h, water was added. The aqueous layer was extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the yellow title compound (900 mg, 1.680 mmol, 94% yield) which was used next step without purification.

Workup

  1. waitAfter 4 h
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×5 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9bac6f527e784b7dbbe7064c9bd8e895
Source dataset
uspto-grants-2016_06
Patent number
US09376396B2

Reaction notes

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