Diisopropylethylamine → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine

HRID 2409075Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[N:13]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[CH:8]([NH2:10])[CH3:9].Cl[C:25]1[N:30]=[C:29]([NH:31][C:32]2[CH:36]=[C:35]([CH:37]3[CH2:39][CH2:38]3)[NH:34][N:33]=2)[CH:28]=[CH:27][N:26]=1.CCN(C(C)C)C(C)C>CC(C(O)C(C)C)C>[CH:37]1([C:35]2[NH:34][N:33]=[C:32]([NH:31][C:29]3[CH:28]=[CH:27][N:26]=[C:25]([NH:10][CH:8]([C:7]4[N:6]=[C:5]5[CH:11]=[CH:12][N:13]([S:14]([C:17]6[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=6)(=[O:16])=[O:15])[C:4]5=[CH:3][C:2]=4[F:1])[CH3:9])[N:30]=3)[CH:36]=2)[CH2:39][CH2:38]1

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (500 mg, 1.5 mmol), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (353 mg, 1.5 mmol), and DIPEA (581 mg, 4.5 mmol) in 2,4-dimethylpentan-3-ol (2 mL) was heated at 135° C. for 15 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by reverse phase chromatography to afford 180 mg (21%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine as a white solid. MS (ESI): m/z=533.3 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-97a4e6d33159487cbfbeb66a42d2b200
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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