Hydrochloric Acid → HCID 178419457, compound

HRID 1785295Notes

Reaction equation

HRID 1785295 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][C:12]2[N:13]=[CH:14][NH:15][CH:16]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[N:17]1([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1.Cl.ClCCl.CO>CO>[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][C:12]2[N:13]=[CH:14][NH:15][CH:16]=2)=[N:4][C:5]([NH:29][C:26]2[CH:25]=[CH:24][C:23]([CH2:22][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:28][CH:27]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7768524-(Pyrrolidin-1-ylmethyl)anilineHCID 21226129Dichloromethane methanolHCID 178478333HCID 178478333, compound

Product 1

HCID 178419457HCID 178419457, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-bromo-4-(2-(1H-imidazol-4-yl)-ethylamino)-2-chloro-pyrimidine (60 mg), 4-pyrrolidin-1-ylmethyl-phenylamine (35 mg) and hydrochloric acid (37% in water, 40 μL) in methanol (2 mL) was refluxed overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution, the organic phase dried (Na2SO4) and evaporated, which gave, after chromatography on silica using dichloromethane/methanol, the title compound (4 mg).

Workup

  1. temperaturewas refluxed overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. dry with materialthe organic phase dried (Na2SO4)
  4. customevaporated
  5. customwhich gave

Sources & evidence

ORD record
ord-4bcf2537d748471a9ecfb404bfad1fc6
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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