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Trifluoroacetate → 4-[(3R)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-N-(1,1-dioxothietan-3-yl)-2-methyl-benzamide

HRID 589646
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HRID 589646 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]2([C:24]([F:27])([F:26])[F:25])[CH2:13][C:12]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[C:16]([CH3:23])[CH:15]=3)=[N:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C([O-])=O.[O:35]=[S:36]1(=[O:41])[CH2:39][CH:38]([NH2:40])[CH2:37]1.ON1C2C=CC=NC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl.C(OCC)(=O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]2([C:24]([F:25])([F:26])[F:27])[CH2:13][C:12]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:40][CH:38]4[CH2:39][S:36](=[O:41])(=[O:35])[CH2:37]4)=[O:20])=[C:16]([CH3:23])[CH:15]=3)=[N:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
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참가 물질

9

반응물 5

HCID 84468TrifluoroacetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 116798243H-1,2,3-Triazolo[4,5-b]pyridine, 1-oxideHCID 552971143-Aminothietane 1,1-dioxideHCID 710777204-[(R)-4-(3,5-Dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzoic acid

생성물 1

HCID 54759939
4-[(3R)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-N-(1,1-dioxothietan-3-yl)-2-methyl-benzamide
수율 35.4%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 4-[(3R)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-benzoic acid (68 mg) in dichloromethane (2.5 mL) was added triethylamine (0.05 mL) at ambient temperature. The solution was then stirred for 5 min under argon and trifluoroacetate salt of 1,1-Dioxo-llambda*6*-thietan-3-ylamine (46 mg) was added. To this solution, 1-hydroxyazabenzotriazole (25 mg) then 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35 mg) were added. The solution was stirred at ambient temperature for 3 days. The reaction mixture was diluted with ethyl acetate and washed with water. The combined organic phases were dried over anhydrous sodium sulfate, the suspension was filtered and the solution was evaporated to give a crude residue which was purified by chromatography on silica gel (eluent: heptane/ethyl acetate, from 1:0 to 6:4) to give 4-[(3R)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-N-(1,1-dioxothietan-3-yl)-2-methyl-benzamide (30 mg) as a white solid.

후처리

  1. stirringThe solution was stirred at ambient temperature for 3 days
  2. washwashed with water
  3. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  4. filtrationthe suspension was filtered
  5. customthe solution was evaporated
  6. customto give a crude residue which
  7. customwas purified by chromatography on silica gel (eluent: heptane/ethyl acetate, from 1:0 to 6:4)

출처 및 근거

ORD 기록
ord-38a0186fd91c4770abe527e450122e39
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09233920B2

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