1-Hydroxybenzotriazole → HCID 178520677, compound

HRID 606399Notes

Reaction equation

HRID 606399 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][C:26](O)=[O:27])[CH:19]=[CH:20][CH:21]=2)=[O:13])[NH:3]1.[NH:29]1[CH:33]=[N:32][C:31]([NH2:34])=[N:30]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][C:26](=[O:27])[NH:34][C:31]3[N:32]=[CH:33][NH:29][N:30]=3)[CH:17]=2)=[O:13])[NH:3]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 135982353HCID 135982353, compoundHCID 178418311HCID 178418311, compound

Product 1

HCID 178520677HCID 178520677, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-{[3-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)phenyl]oxy}butanoic acid obtained in Reference Example 44 (100 mg, 0.262 mmol), 1H-1,2,4-triazol-3-amine (26.4 mg, 0.314 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl-carbodiimide hydrochloride (60.3 mg, 0.314 mmol) and 1-hydroxybenzotriazole (42.5 mg, 0.314 mmol) in DMF (5 mL) was stirred at 40° C. for 5 hr. Water was added to the reaction mixture, and the resulting solid was collected by filtration, washed with water and IPE, and dried to give the title compound as a white powder (95.0 mg, 73%).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water and IPE
  3. customdried

Sources & evidence

ORD record
ord-b2a6ecf547404382976f615a636c7ac0
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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