1-Hydroxybenzotriazole → HCID 58011763, compound

HRID 660927Notes

Reaction equation

HRID 660927 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([OH:20])=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:21][C:22]([F:32])([F:31])[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:27][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[C:23]([C:22]([F:21])([F:31])[F:32])[CH:24]=3)=[O:20])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 759623-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58011831HCID 58011831, compound

Product 1

HCID 58011763HCID 58011763, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30.0 mg (0.102 mmol) of [3-(3-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 104A, 19.7 mg (0.112 mmol) of 3-trifluoromethylbenzylamine and 16.6 mg (0.123 mmol) of HOBt are placed in 0.75 ml of dimethylformamide and treated with 25.5 mg (0.133 mmol) of EDC hydrochloride. This is stirred overnight at room temperature and the reaction solution is purified directly by preparative HPLC [Method 9]. 20 mg (43% of theory) of the target compound are thus obtained.

Workup

  1. customthe reaction solution is purified directly by preparative HPLC [Method 9]
  2. custom20 mg (43% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-c77f478d4daf45c19b17e4b92ec16b5e
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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