HCID 67116320, compound → HCID 69938983, compound

HRID 1525109Notes

Reaction equation

HRID 1525109 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]([C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4I)=[O:18])[CH2:16][CH:11]3[CH2:10]2)[N:3]=1.CC1C=C(C)N=C(N2CC3C[N:41]([C:43]([C:45]4[CH:50]=[CH:49][CH:48]=C(F)C=4I)=O)CC3C2)N=1>[Cu]I.COCCOC>[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]([C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4[C:48]4[CH:49]=[CH:50][CH:45]=[CH:43][N:41]=4)=[O:18])[CH2:16][CH:11]3[CH2:10]2)[N:3]=1

Participants

5

Reactant 2

HCID 67116320HCID 67116320, compoundHCID 67116403HCID 67116403, compound

Product 1

HCID 69938983HCID 69938983, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

The title compound was prepared in a manner analogous to Example 367 substituting (5-(4,6-dimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(4-fluoro-2-iodophenyl)methanone for (5-(4,6-dimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(3-fluoro-2-iodophenyl)methanone, with the addition of catalytic CuI, substituting dioxane for DME, heating 130° C. in microwave for 60 min. The reaction was filtered through celite, rinsed with EtOAc and then concentrated and purified on RP agilent HPLC and fractions lyophilized. MS (ESI) mass calcd. for C24H24FN5O, 417.20; m/z found, 418.2 [M+H]+.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washrinsed with EtOAc
  3. concentrationconcentrated
  4. custompurified on RP agilent HPLC and fractions

Sources & evidence

ORD record
ord-755e124960304784bbbf61a108515d70
Source dataset
uspto-grants-2015_07
Patent number
US09079911B2

Reaction notes

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