Water → HCID 178474974, compound

HRID 2207126Notes

Reaction equation

HRID 2207126 reaction equation
C([O:5][C:6](=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[C:26]([CH2:28][CH2:29][O:30]C)[N:25]=[C:24]([C:32]([CH3:35])([CH3:34])[CH3:33])[N:23]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)(C)(C)C.B(Br)(Br)Br.O.Cl[CH2:43]Cl>>[C:32]([C:24]1[N:23]=[C:22]([N:19]2[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][C@H:11]3[CH2:12][CH2:13][C@H:8]([NH:7][C:6](=[O:5])[CH3:43])[CH2:9][CH2:10]3)[CH2:17][CH2:18]2)[CH:27]=[C:26]([CH2:28][CH2:29][OH:30])[N:25]=1)([CH3:34])([CH3:33])[CH3:35]

Participants

5

Reactant 4

HCID 962WaterHCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 178494789HCID 178494789, compound

Product 1

HCID 178474974HCID 178474974, compound

Procedure

50 mg of trans-N-[4-(2-{4-[2-tert-butyl-6-(2-methoxy-ethyl)-pyrimidin-4-yl]-piperazin-1-yl}-ethyl)-cyclohexyl]-acetamide from example 1 were dissolved in 5 mL of dichloromethane. At −20° C., 1.122 mL of 1 M BBr3 in dichloromethane was added dropwise. The reaction mixture was allowed to warm to room temperature and to stir overnight. Water was added, the organic phase removed and the aqueous phase adjusted to pH 7 with 5% aqueous sodium bicarbonate solution. Ethyl acetate was added, the organic layer removed, and the aqueous phase extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent removed to yield 0.035 mg of crude product which was further purified via silica gel chromatography to yield 0.017 mg of the title compound.

Workup

  1. customthe organic phase removed
  2. additionEthyl acetate was added
  3. customthe organic layer removed
  4. extractionthe aqueous phase extracted three times with ethyl acetate
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed
  8. customto yield 0.035 mg of crude product which
  9. customwas further purified via silica gel chromatography

Sources & evidence

ORD record
ord-e54d68881fa349278c0412dc543cb517
Source dataset
uspto-grants-2016_06
Patent number
US09376396B2

Reaction notes

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