HOAt → 4-[(4-aminopyrimidine-5-yl)carbonyl]amino-N-(2,6-dichlorobenzoyl)-L-phenylalanine methylester

HRID 1393064Notes

Reaction equation

HRID 1393064 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].C(Cl)CCl.Cl.C1C=NC2N(O)N=NC=2C=1.[NH2:40][C:41]1[C:46]([C:47](O)=[O:48])=[CH:45][N:44]=[CH:43][N:42]=1>ClCCl.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:47]([C:46]2[C:41]([NH2:40])=[N:42][CH:43]=[N:44][CH:45]=2)=[O:48])=[CH:21][CH:22]=1)[NH:5][C:6](=[O:15])[C:7]1[C:8]([Cl:14])=[CH:9][CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

7

Reactant 4

HCID 181649HOAtHCID 12014404-Aminopyrimidine-5-carboxylic acidHCID 10384309HCID 10384309, compoundHCID 22619321HCID 22619321, compound

Product 1

HCID 866008844-[(4-aminopyrimidine-5-yl)carbonyl]amino-N-(2,6-dichlorobenzoyl)-L-phenylalanine methylesterYield 10.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

The mixture of N-(2,6-dichlorobenzoyl)-4-amino-L-phenylalanine methylester (1.0 g), EDC/HCl (783 mg), HOAt (555 mg), triethylamine (747 μL), 4-aminopyrimidine-5-carboxylic acid (417 mg) and dichloromethane (15 mL) was stirred overnight. After diluting the mixture with dichloromethane and washing with saturated sodium bicarbonate water, the organic layer thereof was dried over sodium sulfate and concentrated. The residue was washed with dichloromethane to obtain 145 mg of a crude material of the title compound.

Workup

  1. washwashing with saturated sodium bicarbonate water
  2. dry with materialthe organic layer thereof was dried over sodium sulfate
  3. concentrationconcentrated
  4. washThe residue was washed with dichloromethane

Sources & evidence

ORD record
ord-6f06c3795ed5412bb11bdd15724223b0
Source dataset
uspto-grants-2008_03
Patent number
US07345049B2

Reaction notes

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