N-bromobutanimide → HCID 86653752, compound

HRID 2189040Notes

Reaction equation

HRID 2189040 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16]2[C:17]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:23][O:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:39])C(=O)C1>ClC(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16]2[C:17]3[C:24]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[C:23]([Br:39])[O:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 86653751HCID 86653751, compound

Product 1

HCID 86653752HCID 86653752, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

Suspend 100 mg (0.236 mmol) of (+/−)-cis-({3-[(5-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]cyclohexyl}oxy)acetic acid tert-butyl ester in 0.2 ml of tetrachloromethane and add 46.1 mg (0.259 mmol) of NBS. Stir the reaction mixture at 60° C. for a total of 2 h, and add a further 23 mg of NBS after 1 h. After cooling, remove the tetrachloromethane under reduced pressure and purify the residue by preparative RP-HPLC (eluent: acetonitrile/water). 43.6 mg (36.8% of theory) of the target product are obtained.

Workup

  1. temperatureAfter cooling
  2. customremove the tetrachloromethane under reduced pressure
  3. custompurify the residue by preparative RP-HPLC (eluent: acetonitrile/water)
  4. custom43.6 mg (36.8% of theory) of the target product are obtained

Sources & evidence

ORD record
ord-356d5950a43c4e6ea14fa789c2f1c291
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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