1-Hydroxybenzotriazole → HCID 86759837, compound

HRID 586978Notes

Reaction equation

HRID 586978 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]([C:19]([OH:21])=O)[CH2:10][CH2:9]1.C[N:23](CC1C=CC(N)=CC=1)C1CCOCC1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=N>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]([C:19]([NH2:23])=[O:21])[CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 19063555HCID 19063555, compoundHCID 86759838HCID 86759838, compound

Product 1

HCID 86759837HCID 86759837, compoundYield 5.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A catalytic amount of N,N-dimethyl-4-aminopyridine was added to a solution of 7-butoxyethoxyphenyl)-1-[(4-methylthiazol-5-yl)methyl]-2,3-dihydro-1-benzazepine-4-carboxylic acid (150 mg), 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (88 mg) and 1-hydroxybenzotriazole (96 mg) in DMF (15 ml), followed by addition of 1-ethyl-3-(3-dimethylaminopropylcarbodiimide (137 mg). The mixture was stirred under nitrogen atmosphere at room temperature overnight. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was separated and purified with silica gel column chromatography (methanol:ethyl acetate=1:3) to give 7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-tetrahydropyran-5-yl)amino]methyl]phenyl]-1-[(4-methylthiazol-5-yl)methyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 81) (7 mg) as yellow amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was separated
  6. custompurified with silica gel column chromatography (methanol:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-b9e52973e77343aa8286adf829cade9d
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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