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Sodium Chloride → 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[2-(tri-fluoromethyl)phenylmethyl]-acetamide

HRID 660962
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HRID 660962 반응식
[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:11](=[O:17])[N:10]([CH2:18][C:19]([OH:21])=O)[N:9]=1.[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][NH2:27].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[Cl-].[Na+]>O.CN(C=O)C>[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]1[N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:11](=[O:17])[N:10]([CH2:18][C:19]([NH:27][CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[C:23]([F:22])([F:32])[F:33])=[O:21])[N:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 5234Sodium ChlorideHCID 757711-HydroxybenzotriazoleHCID 764472-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 580120612-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid

생성물 1

HCID 58011949
2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[2-(tri-fluoromethyl)phenylmethyl]-acetamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

40.0 mg (0.121 mmol) of 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 249A and 23.4 mg (0.133 mmol) of 2-trifluoromethyl-benzylamine are placed 1.5 ml of DMF and treated with 19.7 mg (0.146 mmol) of HOBt. 30.2 mg (0.158 mmol) of EDC hydrochloride are added and the mixture is stirred overnight at RT. For the workup, the reaction mixture is stirred with about 15 ml of water, saturated with sodium chloride and extracted with ethyl acetate. The organic phase is separated and concentrated, and the residue is dissolved in methanol and purified by preparative HPLC [Method 12]. 26 mg (44% of theory) of the target compound are thus obtained.

후처리

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated
  3. concentrationconcentrated
  4. dissolutionthe residue is dissolved in methanol
  5. custompurified by preparative HPLC [Method 12]
  6. custom26 mg (44% of theory) of the target compound are thus obtained

출처 및 근거

ORD 기록
ord-9e710d365d1c4cf19e5b6fc9354a8176
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084481B2

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