Diisopropylethylamine → HCID 86706478, compound

HRID 919618Notes

Reaction equation

[NH2:1][CH:2]1[CH:7]([CH3:8])[CH2:6][CH2:5][N:4]([C:9](=[O:20])[CH2:10][NH:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)[CH2:3]1.Cl[C:22]1[C:23]2[CH:30]=[CH:29][N:28]([S:31]([C:34]3[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[C:24]=2[N:25]=[CH:26][N:27]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[Cl:19][C:14]1[CH:13]=[C:12]([NH:11][CH2:10][C:9]([N:4]2[CH2:5][CH2:6][CH:7]([CH3:8])[CH:2]([NH:1][C:22]3[C:23]4[CH:30]=[CH:29][N:28]([S:31]([C:34]5[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=5)(=[O:32])=[O:33])[C:24]=4[N:25]=[CH:26][N:27]=3)[CH2:3]2)=[O:20])[CH:17]=[C:16]([Cl:18])[CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(3-amino-4-methylpiperidin-1-yl)-2-(3,5-dichlorophenylamino)ethanone (180 mg, 0.56 mmol) and 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (192 mg, 0.62 mmol) in DMF (5 mL), was added DIEA (0.15 mL, 0.85 mmol) and the reaction mixture was stirred at 60° C. overnight. The reaction mixture was cooled to rt and diluted with EtOAc/water (1:2, 120 mL). The EtOAc layer was separated, dried over Na2SO4 and evaporated in vacuo to give a residue that was purified by column chromatography (silica gel, gradient EtOAc in hexanes) to afford the titled intermediate (120 mg, 35%). LC-MS: m/z [M+1]=587.

Workup

temperatureThe reaction mixture was cooled to rt
customThe EtOAc layer was separated
dry with materialdried over Na2SO4
customevaporated in vacuo
customto give a residue that
customwas purified by column chromatography (silica gel, gradient EtOAc in hexanes)

Sources & evidence

ORD record: ord-b5e42205bb364854be0f5ff35eafa99e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273028B2

Reaction notes

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