1-Hydroxybenzotriazole → HCID 71493652, compound

HRID 1486973Notes

Reaction equation

[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20](O)=[O:21])[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.[CH2:46]([NH:48][CH:49]([C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1)[CH3:50])[CH3:47].C1C=CC2N(O)N=NC=2C=1>ClCCl.CO>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([N:48]([CH2:46][CH3:47])[CH:49]([C:51]3[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=3)[CH3:50])=[O:21])[N:14]=2)[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

Conditions

Temperature: 20 °C

Procedure

In a 3-neck 50 mL round-bottomed flask, (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylic acid (0.2 g, 1.0 eq.) was dissolved in dichloromethane (15 mL) at 0° C. under N2 atmosphere. To this reaction DIPEA (0.088 g, 1.2 eq.), EDC.HCl (0.131 g, 1.2 eq.) and N-ethyl-1-(pyridin-3-yl)ethanamine (0.102 g, 1.2 eq.) was added followed by HOBt (0.104 g, 1.2 eq.). Reaction mixture was stirred at 20° C. for 1 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% methanol: dichloromethane as mobile phase and visualization with UV, SM Rf=0.15 and Product Rf=0.40. Reaction was stirred for 3-4 h and yellow reaction mixture was evaporated on rotary evaporator under reduced pressure to afford 0.4 g of crude compound.

Workup

additionwas added
customReaction mixture
customReaction
stirringwas stirred for 3-4 h
customyellow reaction mixture was evaporated on rotary evaporator under reduced pressure

Sources & evidence

ORD record: ord-9e12b59c09544d24b6b597405b18b6cc
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428490B2

Reaction notes

Loading…