Diisopropylcarbodiimide → 2-[[3-chloro-4-[(3,4-dimethoxyphenyl)methoxy]benzoyl]amino]-N-[2-(2-methoxyphenyl)ethyl]-5-phenoxy-benzamide

HRID 2099962Notes

Reaction equation

HRID 2099962 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH2:6][O:7][C:8]1[CH:32]=[CH:31][C:11]([C:12]([NH:14][C:15]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][C:16]=2[C:17](O)=[O:18])=[O:13])=[CH:10][C:9]=1[Cl:33].C1C=CC2N(O)N=NC=2C=1.C(N=C=NC(C)C)(C)C.[CH3:58][O:59][C:60]1[CH:68]=[CH:67][CH:66]=[CH:65][C:61]=1[CH2:62][CH2:63][NH2:64]>CN(C=O)C>[Cl:33][C:9]1[CH:10]=[C:11]([CH:31]=[CH:32][C:8]=1[O:7][CH2:6][C:5]1[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]([NH:14][C:15]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:20][C:16]=1[C:17]([NH:64][CH2:63][CH2:62][C:61]1[CH:65]=[CH:66][CH:67]=[CH:68][C:60]=1[O:59][CH3:58])=[O:18])=[O:13]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 748962-MethoxyphenethylamineHCID 757711-HydroxybenzotriazoleHCID 577968912-(4-(3,4-Dimethoxybenzyloxy)-3-chlorobenzamido)-5-phenoxybenzoic acid

Product 1

HCID 577968852-[[3-chloro-4-[(3,4-dimethoxyphenyl)methoxy]benzoyl]amino]-N-[2-(2-methoxyphenyl)ethyl]-5-phenoxy-benzamideYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1D (30 mg, 0.056 mmol) in DMF (2 mL) was treated with HOBt (15 mg, 0.11 mmol) and diisopropylcarbodiimide (13 μL, 0.084 mmol) at room temperature. The reaction was stirred for one hour then 2-methoxyphenethylamine was added. The resulting solution was stirred for three hours, concentrated and purified by chromatography (SiO2, 0.5% MeOH in CH2Cl2) to afford 1E (27 mg, 73%).

Workup

  1. stirringThe resulting solution was stirred for three hours
  2. concentrationconcentrated
  3. custompurified by chromatography (SiO2, 0.5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-86463613588b44b4bbd26a2655d0952a
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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