p-Anisoyl chloride → HCID 66641274, compound

HRID 1169814Notes

Reaction equation

HRID 1169814 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 ml 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-dichlorornethane/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 ethyl acetate-dichloromethane 50-50, ethyl acetate-dichloromethane/methanol (95/5) 50-50

Sources & evidence

ORD record
ord-536b8489a30f4ab1b53de1dece032c89
Source dataset
uspto-grants-2010_11
Patent number
US07825119B2

Reaction notes

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