4-Chlorobenzoyl chloride → HCID 89420563, compound

HRID 407110Notes

Reaction equation

HRID 407110 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[NH2:15])[C:4]([CH3:16])=[N:3]1.C(N(CC)C(C)C)(C)C.[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH2:15][C:9]1[CH:10]=[C:11]([NH:14][C:31]([C:30]2[CH:34]=[CH:35][C:27]([Cl:26])=[CH:28][CH:29]=2)=[O:32])[CH:12]=[CH:13][C:8]=1[C:5]1[C:4]([CH3:16])=[N:3][N:2]([CH3:1])[C:6]=1[CH3:7]

Participants

6

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 67468824HCID 67468824, compound

Product 1

HCID 89420563HCID 89420563, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 76 (119.4 mg, 0.55 mmol) in CH2Cl2 (20 ml) was added N,N-diisopropylethylamine (DIEA, 258 mg, 348 μL, 2 mmol), 4-dimethylaminopyridine (DMAP, 0.6 mg, 0.05 mmol). The 4-chlorobenzoyl chloride (96 mg, 0.55 mmol) was dropped into above solution. The mixture was stirred for 2 h at room temperature. The reaction was quenched with saturated NaHCO3 (40 ml) and extracted with EtOAc. The dicarboxamide was hydrolyzed with 1M NaOH in THF and MeOH (1:1). The product was purified by HPLC and afforded 77 (49 mg, 25%) as yellow solid. LC-MS: calcd. for C19H19ClN4O: 355 (M+1).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 (40 ml)
  2. extractionextracted with EtOAc
  3. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-a123bf3fdbbe4b5c88c0e233a4e629ab
Source dataset
uspto-grants-2014_06
Patent number
US08754219B2

Reaction notes

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