1-Hydroxybenzotriazole → HCID 58011694, compound

HRID 660944Notes

Reaction equation

HRID 660944 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]=[CH2:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([OH:20])=O)[N:9]=2)=[CH:4][CH:3]=1.[F:21][C:22]([F:34])([F:33])[C:23]1[CH:24]=[C:25]([C:29]([NH2:32])([CH3:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:13][CH:14]=[CH2:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:32][C:29]([CH3:31])([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:33])[F:34])[CH:24]=3)[CH3:30])=[O:20])[N:9]=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 58012168HCID 58012168, compound

Product 1

HCID 58011694HCID 58011694, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.98 g (6.74 mmol) of [3-(4-chlorophenyl)-4-allyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 218A and 1.51 g (7.42 mmol) of 1-methyl-1-[(3-trifluoromethyl)phenyl]-ethylamine from Example 1A are placed in 50 ml of DMF and treated with 1.09 g (8.09 mmol) of HOBt. After 10 mins' stirring, 1.68 g (8.76 mmol) of EDC hydrochloride are added and the mixture is stirred overnight at RT. For the workup, the reaction mixture is stirred with 500 ml of water. Next, the resulting precipitate is suction-filtered, washed with water and dried under high vacuum. 2.41 g (75% of theory) of the target compound are thus obtained.

Workup

  1. stirringthe mixture is stirred overnight at RT
  2. filtrationNext, the resulting precipitate is suction-filtered
  3. washwashed with water
  4. customdried under high vacuum
  5. custom2.41 g (75% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-660423247b444fc9ae19b8670bb929f1
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

Loading…