Diisopropylethylamine → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl)pyrimidine-2,4-diamine

HRID 2409073Notes

Reaction equation

[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([CH2:20][NH2:21])[C:14]=2[CH:13]=[N:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl[C:23]1[N:28]=[C:27]([NH:29][C:30]2[CH:34]=[C:33]([CH:35]3[CH2:37][CH2:36]3)[NH:32][N:31]=2)[CH:26]=[CH:25][N:24]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH:35]1([C:33]2[NH:32][N:31]=[C:30]([NH:29][C:27]3[CH:26]=[CH:25][N:24]=[C:23]([NH:21][CH2:20][C:15]4[C:14]5[CH:13]=[N:12][N:11]([S:1]([C:4]6[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=6)(=[O:3])=[O:2])[C:19]=5[CH:18]=[CH:17][N:16]=4)[N:28]=3)[CH:34]=2)[CH2:37][CH2:36]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (1-tosyl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanamine (300 mg, 1.3 mmol), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (258 mg, 1.05 mmol), and DIPEA (0.5 mL) in IPA (2 mL) was heated at 120° C. overnight. The reaction mixture was concentrated under reduced pressure to afford 400 mg (61%) of crude N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl)pyrimidine-2,4-diamine as yellow oil. MS (ESI): m/z=502.3 [M+1]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-00db247308b841b69f5361733df79b29
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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