Triethylamine → 1H-Benzoimidazole-2-carboxylic acid [4-(3-oxo-morpholin-4-yl)-phenyl]-amide

HRID 18527

Reaction equation

HRID 18527 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([OH:12])=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][C:21]2=[O:26])=[CH:16][CH:15]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.CCN(CC)CC>C(Cl)Cl.O>[O:26]=[C:21]1[CH2:22][O:23][CH2:24][CH2:25][N:20]1[C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:10]([C:2]2[NH:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[O:12])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2332402-Benzimidazolecarboxylic acidHCID 111948544-(4-Aminophenyl)morpholin-3-one

Product 1

HCID 860098191H-Benzoimidazole-2-carboxylic acid [4-(3-oxo-morpholin-4-yl)-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg 1H-Benzoimidazole-2-carboxylic acid and 118 mg 4-(4-Amino-phenyl)-morpholin-3-one in 2 mL DCM, 157 mg BOP-Cl and 0.3 mL NEt3 were added and the mixture was stirred for 16 h at RT. Then, after the reaction mixture was diluted with 20 mL water, the precipitated product was collected by filtration. The crude product was subjected to the next reaction step without further purification. Yield: 122 mg.

Workup

  1. filtrationthe precipitated product was collected by filtration
  2. customThe crude product was subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-9c72ab4d86a7485eb49a9fb83d92fa99
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Linked notes

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