HCID 66970588, compound → HCID 58397052, compound

HRID 1361693Notes

Reaction equation

HRID 1361693 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:34])[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([O:21][C:22]3[C:27]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][N:29]=4)=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]>CO.CCOC(C)=O.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)=[O:34])=[CH:13][C:14]=1[O:21][C:22]1[C:27]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][N:29]=2)=[CH:26][CH:25]=[CH:24][N:23]=1

Participants

5

Reactant 1

HCID 66970588HCID 66970588, compound

Product 1

HCID 58397052HCID 58397052, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-isopropylphenyl)-4-nitro-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzamide (0.090 g, 0.20 mmol) in MeOH (3 mL) and EtOAc (3 mL) was added NH4OAc (0.030 g) and Pd/C (10%) (0.020 g). The reaction was capped with a septum, and positive H2 pressure was applied with a balloon/needle. The reaction was stirred for several hours, at which point LCMS indicated formation of product. The mixture was filtered through sand/celite, concentrated onto silica gel, and chromatographed with 8:8:8:1 t-BuOMe:hexanes:CH2Cl2:MeOH to afford 4-amino-N-(3-isopropylphenyl)-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzamide as a yellow solid. MS m/z=426 [M+H]+. Calc'd for C25H23N5O2: 425.49.

Workup

  1. customThe reaction was capped with a septum, and positive H2 pressure
  2. filtrationThe mixture was filtered through sand/celite,
  3. concentrationconcentrated onto silica gel
  4. customchromatographed with 8:8:8:1 t-BuOMe

Sources & evidence

ORD record
ord-6aff60daad4145b79384cac3fd804803
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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