Diisopropylethylamine → HCID 86694765, compound

HRID 475314Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[F:17][C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][N:24]2C2CCCCO2)=[C:20]([CH2:33][NH:34][CH2:35][CH2:36][N:37](C)[C:38](=O)OC(C)(C)C)[CH:19]=1.CCN(C(C)C)C(C)C.Cl.O1CCOCC1>CCCCO>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([N:34]([CH2:33][C:20]4[CH:19]=[C:18]([F:17])[CH:26]=[C:25]5[C:21]=4[CH:22]=[N:23][NH:24]5)[CH2:35][CH2:36][NH:37][CH3:38])[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 115 °C

Procedure

A vial was charged with 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (100 mg, 0.42 mmol), tert-butyl (2-(((6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methyl)amino)ethyl)(methyl)carbamate (207 mg, 0.51 mmol), DIPEA (0.22 mL, 1.27 mmol) and n-BuOH (0.9 mL), sealed and heated at 115° C. for 4 d. The reaction mixture was then cooled to RT and 4N HCl/dioxane (1.06 mL, 4.24 mmol) was added. The reaction mixture was stirred at RT for 16 h then concentrated nvacuo. The crude mixture was purified by preparative HPLC to afford 22.4 mg (13%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((6-fluoro-1H-indazol-4-yl)methyl)-N2-(2-(methylamino)ethyl)pyrimidine-2,4-diamine (II-47).

Workup

customsealed
temperatureThe reaction mixture was then cooled to RT
concentrationthen concentrated nvacuo
customThe crude mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-b7983ec8916d46b0abba4bd66b93475e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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