Diisopropylethylamine → tert-butyl 4-((1R)-1-(5-cyano-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamino)ethyl)piperidine-1-carboxylate

HRID 40846Notes

Reaction equation

HRID 40846 reaction equation
P(OCC)(OCC)(O[C:4]1[N:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=3)[N:12]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:11]=2)[C:7]([C:33]#[N:34])=[CH:6][N:5]=1)=O.[NH2:41][C@@H:42]([CH:44]1[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]1)[CH3:43].C(N(C(C)C)CC)(C)C>C1COCC1.C(OCC)(=O)C>[C:33]([C:7]1[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=3)[N:12]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=3)(=[O:24])=[O:25])[CH:11]=2)=[N:9][C:4]([NH:41][C@@H:42]([CH:44]2[CH2:45][CH2:46][N:47]([C:50]([O:52][C:53]([CH3:54])([CH3:56])[CH3:55])=[O:51])[CH2:48][CH2:49]2)[CH3:43])=[N:5][CH:6]=1)#[N:34]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 594143445-cyano-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo [2,3-b]pyridin-3-yl)pyrimidin-2-yl diethyl phosphateHCID 59414623tert-butyl 4-((1R)-1-aminoethyl)piperidine-1-carboxylate

Product 1

HCID 59414400tert-butyl 4-((1R)-1-(5-cyano-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamino)ethyl)piperidine-1-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-cyano-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-yl diethyl phosphate (200 mg, 0.3359 mmol) was treated with a solution of (R)-tert-butyl 4-(1-aminoethyl)piperidine-1-carboxylate (76.70 mg, 0.3359 mmol) in THF (2 mL), and diisopropylethylamine (70.22 μL, 0.4031 mmol). The reaction mixture was stirred at room temperature for 24 hours. The crude mixture was diluted with ethyl acetate and washed with aqueous NaHCO3. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified on silica gel by flash column chromatography to afford the title compound as a colourless glass (188 mg, 84% yield).

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-c4205d7b67aa45c0a7fe8b2cccc865cd
Source dataset
uspto-grants-2013_09
Patent number
US08530489B2

Reaction notes

Loading…