Nitrogen → HCID 46236233, compound

HRID 2090511Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH3:26])[N:8]([C:12]3[CH:17]=[C:16]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[N:15]=[C:14]([NH2:25])[N:13]=3)[CH2:9]2)=[CH:4][CH:3]=1.ClCCl.C(=O)([O-])[O-].[K+].[K+].[N:36]#[N:37]>O1CCOCC1.O>[CH3:24][N:21]1[CH2:20][CH2:19][N:18]([C:16]2[CH:17]=[C:12]([N:8]3[CH:7]([CH3:26])[CH2:6][C:5]4[C:10](=[CH:11][C:2]([C:2]5[CH:3]=[CH:4][N:37]([CH2:11][C:10]6[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=6)[N:36]=5)=[CH:3][CH:4]=4)[CH2:9]3)[N:13]=[C:14]([NH2:25])[N:15]=2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 110 °C

Procedure

The residue was dissolved in 1,4-dioxane (0.50 mL) and water (0.10 mL), to this solution was added 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (0.018 g, 0.043 mmol, Peak 1, Example 49, Step 7), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (1.76 mg, 0.00216 mmol), potassium carbonate (11.9 mg, 0.0862 mmol) and the mixture was vacuumed and refilled with N2 for 3 times. The reaction was stirred at 110° C. overnight. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=496.3.

Workup

customThe mixture was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record: ord-0b509884e55f4c93adbca338b86756ee
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436008B2

Reaction notes

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