Water → HCID 86636624, compound

HRID 2281505Notes

Reaction equation

HRID 2281505 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]1.O.CCOC(C)=O>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][CH:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]2)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 5458091-BOC-3-AminopiperidineHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86636624HCID 86636624, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (233 mg, 0.681 mmol), 3-amino-1-N-Boc-piperidine (136 mg, 0.680 mmol) and TEA (0.200 mL, 1.44 mmol) in dioxane (5 mL) was stirred at 70° C. for 20 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give tert-butyl 3-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (251 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialwith 5% NaHCO3, dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09705b57b1e24446a383677fbfb9edf7
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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