Dimethylformamide → HCID 59580003, compound

HRID 2279617Notes

Reaction equation

HRID 2279617 reaction equation
[C:1]12([CH2:11][NH:12][C:13]([C:15]3[C:16]([CH3:28])=[N:17][N:18]([C:20]4[N:25]=[C:24](Br)[C:23]([CH3:27])=[CH:22][N:21]=4)[CH:19]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CCOC(C)=O.[CH3:35][N:36](C=O)C>[Cl-].[Na+].O.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]12([CH2:11][NH:12][C:13]([C:15]3[C:16]([CH3:28])=[N:17][N:18]([C:20]4[N:25]=[C:24]([C:35]#[N:36])[C:23]([CH3:27])=[CH:22][N:21]=4)[CH:19]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 25226166HCID 25226166, compound

Product 1

HCID 59580003HCID 59580003, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 1-(4-bromo-5-methyl-pyrimidin-2-yl)-3-methyl-1H-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide (1.05 g, 2.4 mmol), zinc cyanide (328 mg, 2.8 mmol) and Pd(PPh3)4 (240 mg) in DMF (12 mL) is heated at 90° C. for 12 h. The mixture is cooled to RT and EtOAc and brine are added. The mixture is filtered through Celite, and the organic layer is separated, washed with brine, dried and evaporated. Purification by flash chromatography, eluting with a mixture of 5% MeOH and 1% TEA in DCM, affords the title compound. MS (M+1)=391.27; RT=1.34 min. *IC50.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. customthe organic layer is separated
  3. washwashed with brine
  4. customdried
  5. customevaporated
  6. customPurification by flash chromatography
  7. washeluting with a mixture of 5% MeOH and 1% TEA in DCM

Sources & evidence

ORD record
ord-a25bdce71588415babe76cdc5be60e79
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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