Triethylamine → HCID 11566840, compound

HRID 2192180Notes

Reaction equation

HRID 2192180 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[C:14]([F:16])[C:13]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[NH:24][CH:25]=[C:26]([CH3:27])[C:19]=34)=[C:12]([F:28])[CH:11]=2)[CH:3]=1.C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[F:16][C:14]1[CH:15]=[C:10]([NH:9][C:4]2[CH:3]=[CH:2][N:7]=[C:6]([NH2:8])[N:5]=2)[CH:11]=[C:12]([F:28])[C:13]=1[O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]2[NH:24][CH:25]=[C:26]([CH3:27])[C:19]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11524200TC-S 7001HCID 178418361HCID 178418361, compound

Product 1

HCID 11566840HCID 11566840, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

50 mg (0.12 mmol) of 6-chloro-N4-{3,5-difluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidine-2,4-diamine are dissolved in 10 ml of ethanol. 35 μl (0.25 mmol) of triethylamine and 26 mg (0.02 mmol) of 10% palladium-on-carbon are added, and the mixture is hydrogenated under atmospheric pressure in a hydrogen atmosphere overnight. The mixture is then filtered through Celite®, and the celite is washed with methanol. The solvent is removed under reduced pressure and the crude product is purified by preparative HPLC.

Workup

  1. filtrationThe mixture is then filtered through Celite®
  2. washthe celite is washed with methanol
  3. customThe solvent is removed under reduced pressure
  4. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-98b00d85b8334b458123237de0d91d2b
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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