Triethylamine → HCID 67351564, compound

HRID 1672859Notes

Reaction equation

HRID 1672859 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=O)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:26]=1.Cl.[CH2:28]([N:30]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.Cl.CN.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH3:28][NH:30][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][CH:25]=[C:17]([N:14]2[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]3[N:26]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=3[C:15]2=[O:16])[CH:18]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 67350552HCID 67350552, compound

Product 1

HCID 67351564HCID 67351564, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid (364 mg, 0.982 mmol) obtained in Step 1 of Example 56 was dissolved in DMF (10 mL), and the mixture was stirred at room temperature for 3.5 hours after adding 1-ethyl-3-(3dimethylaminopropyl)carbodiimide hydrochloride (207 mg, 1.08 mmol), 1-hydroxybenzotriazole.monohydrate (166 mg, 1.08 mmol), methylamine hydrochloride (100 mg, 1.47 mmol), and triethylamine (0.204 mL, 1.47 mmol). The mixture was diluted by addition of ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (S)—N-methyl-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzamide (390 mg, 91%).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6d9b62d08ee6401ea650b95aa159c70e
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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