1-Hydroxybenzotriazole → HCID 67350091, compound

HRID 1672829Notes

Reaction equation

HRID 1672829 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]([C:23]4[O:24][CH:25]=[C:26]([C:28]([OH:30])=O)[N:27]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:31]=1.O.N.Cl.C([N:37]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[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]([C:23]4[O:24][CH:25]=[C:26]([C:28]([NH2:37])=[O:30])[N:27]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:31]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12896473Azane;hydrateHCID 67348673HCID 67348673, compound

Product 1

HCID 67350091HCID 67350091, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-[3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-4-carboxylic acid (300 mg, 0.685 mmol) obtained in Step 1 of Example 124 was dissolved in DMF (7 mL), and the mixture was stirred at room temperature for 2 hours after adding 28% ammonia water (0.0830 mL, 1.37 mmol), 1-ethyl-3-(3dimethylaminopropyl)carbodiimide hydrochloride (263 mg, 1.37 mmol), and 1-hydroxybenzotriazole.monohydrate (210 mg, 1.37 mmol). Thereafter, ethyl acetate was added to the mixture, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give (S)-2-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-4-carboxamide (261 mg, 87%).

Workup

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe residue obtained upon concentration under reduced pressure
  4. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7bf888f86e7e483f875da0bcbc4c65a8
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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