Diisopropylethylamine → HCID 67969468, compound

HRID 571699Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.Cl[C:16]1[C:17]2[CH:24]=[CH:23][NH:22][C:18]=2[N:19]=[CH:20][N:21]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[N:19]1[C:18]2[NH:22][CH:23]=[CH:24][C:17]=2[C:16]([N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:2]2)=[N:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl piperidin-3-ylcarbamate compound (5.0 g, 25 mmol) and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.75 g, 25 mmol) in DMF (50 mL) was added DIEA (4.2 mL, 3.1 g, 25 mmol) and the solution was stirred at 100° C. for 4 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography to give tert-butyl 1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-ylcarbamate. To a solution of tert-butyl 1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-ylcarbamate (6.3 g, 20 mmol) in dioxane (50 ml) was added 4.0 N HCl (50 mL, 200 mmol) and stirred at rt. After several hours, the reaction mixture was concentrated in vacuo to give compound 33.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-aa72c85b17704567a2b004f9fc3287a1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029359B2

Reaction notes

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