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

HRID 2409067Notes

Reaction equation

[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([CH:20]([NH2:22])[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl[C:24]1[N:29]=[C:28]([NH:30][C:31]2[CH:35]=[C:34]([CH:36]3[CH2:38][CH2:37]3)[NH:33][N:32]=2)[CH:27]=[CH:26][N:25]=1.CCN(C(C)C)C(C)C>CC(C(O)C(C)C)C>[CH:36]1([C:34]2[NH:33][N:32]=[C:31]([NH:30][C:28]3[CH:27]=[CH:26][N:25]=[C:24]([NH:22][CH:20]([C:15]4[C:14]5[CH:13]=[CH: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)[CH3:21])[N:29]=3)[CH:35]=2)[CH2:38][CH2:37]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of (±)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine (referential example 11) (800 mg, 2.54 mmol), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-pyrimidin-4-amine (500 mg, 2.12 mmol), and DIPEA (820 mg, 6.36 mmol) in 2,4-dimethylpentan-3-ol (10 mL) in a sealed tube under nitrogen was stirred at 140° C. for 18 h. The crude product was purified by preparative HPLC to afford 563 mg (51.7%) of (±)—N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethyl)pyrimidine-2,4-diamine as a yellow solid (563 mg, 51.7%): MS (ESI) m/z: 515.2 [M+1]+

Workup

customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-6046fe36c3e04dd99c1e13091fedc076
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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