Dimethylformamide → HCID 69425813, compound

HRID 1182358Notes

Reaction equation

HRID 1182358 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:32]=[N:31][C:18]3[N:19]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:20][CH2:21][C:22]([C:24](O)=[O:25])=[CH:23][C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH3:44][N:45]([CH2:52][C:53]1[CH:59]=[CH:58][C:56]([NH2:57])=[CH:55][CH:54]=1)[CH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>ClCCl.N1C=CC=CC=1.O>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:32]=[N:31][C:18]3[N:19]([CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:20][CH2:21][C:22]([C:24]([NH:57][C:56]4[CH:58]=[CH:59][C:53]([CH2:52][N:45]([CH3:44])[CH:46]5[CH2:51][CH2:50][O:49][CH2:48][CH2:47]5)=[CH:54][CH:55]=4)=[O:25])=[CH:23][C:17]=3[CH:16]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 69423680HCID 69423680, compound

Product 1

HCID 69425813HCID 69425813, compoundYield 87.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[4-(2-butoxyethoxy)phenyl]-9-isobutyl-8,9-dihydro-7H-pyrido[2,3-b]azepine-6-carboxylic acid (130 mg) in dichloromethane (10 ml) were added a drop of DMF. Then, oxalyl chloride (0.034 ml) was added thereto, and the mixture was stirred for 1 hour under a nitrogen atmosphere. The resulting solution was added dropwise to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (85 mg) in pyridine (10 ml) at 0° C. under a nitrogen atmosphere. The resulting mixture was stirred at room temperature under a nitrogen atmosphere overnight. Then, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resulting residue was purified by basic silica gel column chromatography (methanol:ethyl acetate=1:8) to give 3-[4-(2-butoxyethoxy)phenyl]-9-isobutyl-N-[4-[[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-8,9-dihydro-7H-pyrido[2,3-b]azepine-6-carboxamide (167 mg) (Compound 4) as a yellow amorphous material.

Workup

  1. stirringThe resulting mixture was stirred at room temperature under a nitrogen atmosphere overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by basic silica gel column chromatography (methanol:ethyl acetate=1:8)

Sources & evidence

ORD record
ord-8c61f1eceea94f26bf39b562d9dfca72
Source dataset
uspto-grants-2007_10
Patent number
US07288654B2

Reaction notes

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