Piperidine → HCID 131735535, compound

HRID 522423Notes

Reaction equation

HRID 522423 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:7][C:8]1[C:9]([O:23][C@H:24]2[CH2:70][N:27]3[C:28](=[O:69])[C@@H:29]([NH:48][C:49]([O:51][C@@H:52]4[CH2:54][C@H:53]4[CH2:55][CH2:56][CH2:57]/[CH:58]=[CH:59]/[B:60]4[O:64][C:63]([CH3:66])([CH3:65])[C:62]([CH3:68])([CH3:67])[O:61]4)=[O:50])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH:36][C@@H:37]4[CH2:42][C@@:38]4([C:43]([O:45][CH2:46][CH3:47])=[O:44])[NH:39][C:40](=[O:41])[C@@H:26]3[CH2:25]2)=[N:10][C:11]2[C:16]([C:17]=1[O:18][CH2:19][CH2:20][CH2:21]Br)=[CH:15][CH:14]=[CH:13][CH:12]=2>CS(C)=O>[Br:7][C:8]1[C:9]([O:23][C@H:24]2[CH2:70][N:27]3[C:28](=[O:69])[C@@H:29]([NH:48][C:49]([O:51][C@@H:52]4[CH2:54][C@H:53]4[CH2:55][CH2:56][CH2:57]/[CH:58]=[CH:59]/[B:60]4[O:61][C:62]([CH3:68])([CH3:67])[C:63]([CH3:66])([CH3:65])[O:64]4)=[O:50])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH:36][C@@H:37]4[CH2:42][C@@:38]4([C:43]([O:45][CH2:46][CH3:47])=[O:44])[NH:39][C:40](=[O:41])[C@@H:26]3[CH2:25]2)=[N:10][C:15]2[C:16]([C:17]=1[O:18][CH2:19][CH2:20][CH2:21][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 8082PiperidineHCID 131735536HCID 131735536, compound

Product 1

HCID 131735535HCID 131735535, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Piperidine (317 μl) was added to a solution of bromide from Step 1 (326 mg) in DMSO (2 mL) and the resulting mixture was stirred for 2 hours at room temperature. The reaction was quenched with water and extracted with ethyl acetate (3×). The combined organic fractions were washed with water then brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (ISCO reverse phase, 0 to 95% acetonitrile in water) to give the title compound (262 mg) as a mixture with the boronic acid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic fractions were washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (ISCO reverse phase, 0 to 95% acetonitrile in water)

Sources & evidence

ORD record
ord-0ef219c0cc714d1faabfa32c36dca076
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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