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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
ノート
印刷プレビュー

反応式

HRID 589646 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 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
収率 35.4%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-38a0186fd91c4770abe527e450122e39
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09233920B2

反応ノート

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