1,4-Dioxane → HCID 67116616, compound

HRID 244011Notes

Reaction equation

HRID 244011 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:13][CH:12]3[CH2:14][N:15]([CH:17]=[O:18])[CH2:16][CH:11]3[CH2:10]2)[N:3]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[N:20]1.O1[CH2:29][CH2:28]OCC1>O.[Cu]I>[N:19]1[N:20]([C:29]2[C:28]([C:17]([N:15]3[CH2:14][CH:12]4[CH:11]([CH2:10][N:9]([C:4]5[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=5)[CH2:13]4)[CH2:16]3)=[O:18])=[CH:6][CH:7]=[CH:2][N:3]=2)[N:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 86669170HCID 86669170, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 67116616HCID 67116616, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

To a solution of 2-bromopyridin-3-yl)(5-(4,6-dimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone (Example 234) (150 mg, 0.37 mmol), 1H-1,2,3 triazole (43 μL, 0.75 mmol), CsCO3 (247 mg, 0.75 mmol), in H2O (2 μL) and 1,4 dioxane (2 mL) was added (R,R)-(−)-N,N′-dimethyl-1,2-cyclohexyldiamine (12 μL, 0.75 mmol) and CuI (3.5 mg, 0.86 mmol). The reaction mixture was irradiated in a microwave reactor at 160° C. for 2 h. The resulting solution was filtered through Celite®, washed with DCM, and concentrated. Purification (FCC)(MeOH(NH3)/DCM) gave the title compound (8 mg, 6%). MS (ESI): mass calculated for C20H22N8O, 390.19; m/z found 391.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.65 (dd, J=4.8, 1.8, 1H), 7.83 (dt, J=13.3, 6.6, 2H), 7.43 (dt, J=7.6, 4.5, 1H), 6.38-6.23 (m, 2H), 4.02-3.28 (m, 6H), 3.10-3.06 (m, 4H), 2.42-2.22 (m, 6H).

Workup

  1. customThe reaction mixture was irradiated in a microwave reactor at 160° C. for 2 h
  2. filtrationThe resulting solution was filtered through Celite®
  3. washwashed with DCM
  4. concentrationconcentrated
  5. customPurification (FCC)(MeOH(NH3)/DCM)

Sources & evidence

ORD record
ord-142f669d1fdb4698a024f49b401359ba
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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