Water → tert-butyl 3-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)azepane-1-carboxylate

HRID 919605Notes

Reaction equation

[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.Cl[C:17]1[C:18]2[CH:25]=[CH:24][N:23]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:19]=2[N:20]=[CH:21][N:22]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[S:26]([N:23]1[C:19]2[N:20]=[CH:21][N:22]=[C:17]([NH:1][CH:2]3[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]3)[C:18]=2[CH:25]=[CH:24]1)([C:29]1[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=1)(=[O:27])=[O:28]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of tert-butyl 3-aminoazepane-1-carboxylate (1 g, 4.7 mmol), 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (3.1 g, 5.1 mmol) in DMF (10 mL) was added DIEA (1.2 mL, 7.0 mmol) and the reaction mixture was heated to 90° C. for 3 h. The reaction was cooled to rt and diluted with ice cooled water (50 mL). The mixture was extracted with EtOAc (3×100 mL), the EtOAc layers were combined, dried over Na2SO4 and evaporated in vacuo to give the crude product that was purified by column chromatography (silica gel, gradient 0-20% EtOAc hexane) to afford the titled intermediate (1.4 g, 89%). LC-MS: m/z [M+1]=486.

Workup

temperatureThe reaction was cooled to rt
additiondiluted with ice
extractionThe mixture was extracted with EtOAc (3×100 mL)
dry with materialdried over Na2SO4
customevaporated in vacuo
customto give the crude product that
customwas purified by column chromatography (silica gel, gradient 0-20% EtOAc hexane)

Sources & evidence

ORD record: ord-158423ec14724027950244f21081bdd2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273028B2

Reaction notes

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