1-Hydroxybenzotriazole → HCID 58012169, compound

HRID 660906Notes

Reaction equation

HRID 660906 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:17])[N:11]([CH2:13][C:14]([OH:16])=O)[CH:12]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[F:40][C:41]([F:53])([F:52])[C:42]1[CH:43]=[C:44]([C:48]([NH2:51])([CH3:50])[CH3:49])[CH:45]=[CH:46][CH:47]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:17])[N:11]([CH2:13][C:14]([NH:51][C:48]([CH3:50])([C:44]3[CH:45]=[CH:46][CH:47]=[C:42]([C:41]([F:40])([F:52])[F:53])[CH:43]=3)[CH3:49])=[O:16])[CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 194252732-[3-(Trifluoromethyl)phenyl]propan-2-amineHCID 58011978HCID 58011978, compound

Product 1

HCID 58012169HCID 58012169, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

318 mg (1.26 mmol) of [4-(4-chlorophenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid from Example 233A are placed in 10 ml DMF and treated with 221 mg (1.64 mmol) of HOBt and 314 mg (1.64 mmol) of EDC hydrochloride. After 10 mins' stirring, 332 mg (1.64 mmol) of 1-methyl-1-[(3-trifluoromethyl)phenyl]ethylamine from Example 1A are added and the mixture is stirred overnight at room temperature. For the workup, the reaction mixture is stirred with 100 ml water. Next, the resulting precipitate is suction-filtered, washed with water and dried under high vacuum. Further purification is effected by preparative HPLC [Method 10]. 209 mg (38% of theory) of the target compound are thus obtained.

Workup

  1. stirringthe mixture is stirred overnight at room temperature
  2. filtrationNext, the resulting precipitate is suction-filtered
  3. washwashed with water
  4. customdried under high vacuum
  5. customFurther purification
  6. custom209 mg (38% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-3f3a987169e14c18a32a7c1498736b38
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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