p-Anisoyl chloride → HCID 66641274, compound

HRID 2261171Notes

Reaction equation

HRID 2261171 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.N[CH:13]([CH2:21][NH:22][C:23]1[C:28]([CH3:29])=[C:27]([N:30]2[CH2:35][CH2:34][CH:33]([C:36]3[CH:45]=[CH:44][C:43]4[CH2:42][CH2:41][CH2:40][NH:39][C:38]=4[N:37]=3)[CH2:32][CH2:31]2)[N:26]=[CH:25][N:24]=1)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>ClCCl.N1C=CC=CC=1>[CH3:29][C:28]1[C:23]([NH:22][CH2:21][CH:13]([C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:24][CH:25]=[N:26][C:27]=1[N:30]1[CH2:35][CH2:34][CH:33]([C:36]2[CH:45]=[CH:44][C:43]3[CH2:42][CH2:41][CH2:40][NH:39][C:38]=3[N:37]=2)[CH2:32][CH2:31]1

Participants

5

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 66641074HCID 66641074, compound

Product 1

HCID 66641274HCID 66641274, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

40 mg (0.233 mmoles) of 4-methoxy-benzoyl chloride in solution in 3 ml of dichloromethane is added to a mixture of 109 mg (0.233 mmoles) of tert-butyl 2-amino-3-{5-methyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino}-propionate in solution in 6 ml of dichloromethane and 650 μl of pyridine. The reaction mixture is stirred at ambient temperature for 1 hour. Then, the solvent is evaporated off under reduced pressure (2 kPa) and the residue is chromatographed on silica gel with the following eluent: ethyl acetate-dichloromethane 50-50, ethyl acetate-dichloromethane/methanol (95/5) 50-50 then finishing with ethyl acetate-dichloromethane/methanol (9/1) 50-50. 98 mg of expected product is obtained.

Workup

  1. customThen, the solvent is evaporated off under reduced pressure (2 kPa)
  2. customthe residue is chromatographed on silica gel with the following eluent

Sources & evidence

ORD record
ord-78bb04f12eb6439a90a479bec3493ee0
Source dataset
uspto-grants-2010_12
Patent number
US07846932B2

Reaction notes

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