Hydrochloric Acid → HCID 73056322, compound

HRID 1779116Notes

Reaction equation

HRID 1779116 reaction equation
[NH2:1][CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][C:26]([NH2:28])=[O:27])[C:14]([Cl:29])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].[C:30](OC(=O)C)(=[O:32])[CH3:31].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:30]([NH:1][CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][C:26]([NH2:28])=[O:27])[C:14]([Cl:29])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3])(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 73056321HCID 73056321, compound

Product 1

HCID 73056322HCID 73056322, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 2-(2-(2-(2-((3-(1-aminoethyl)phenyl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)acetamide (38) (0.045 g, 0.11 mmol) in pyridine (3 mL) containing acetic anhydride (62 μL, 0.66 mmol) and 4-dimethylaminopyridine (2.6 mg, 0.022 mmol) was stirred at room temperature for 22 hours under a nitrogen atmosphere. The mixture was acidified with 1 M hydrochloric acid (30 mL) and extracted with DCM (3×20 mL). The combined organic phases were washed with water, brine, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was adsorbed onto silica gel and the product was purified by column chromatography (CombiFlash Rf, 4 g SiO2 Cartridge, 0-10% MeOH in DCM) to yield the title compound (39) as a white solid (0.035 g, 70%). LCMS-B: rt 6.20 min; m/z 452 [M+H]+.

Workup

  1. extractionextracted with DCM (3×20 mL)
  2. washThe combined organic phases were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated in vacuo
  5. customthe product was purified by column chromatography (CombiFlash Rf, 4 g SiO2 Cartridge, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-dd5a9ac1bc3047d8b46376c3c79cc98d
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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