Triethylamine → HCID 178477280、化合物

HRID 724333ノート

反応式

HRID 724333 の反応式
[CH2:1]([S:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][C:8]1[N:16]=[CH:15][C:14]([F:17])=[CH:13][C:9]=1[C:10]([OH:12])=O)[CH3:2].Cl.[NH2:22][CH:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][OH:33])[CH2:25][CH2:24]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH2:1]([S:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][C:8]1[N:16]=[CH:15][C:14]([F:17])=[CH:13][C:9]=1[C:10]([NH:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([NH:29][C:30](=[O:36])[C:31]([CH3:34])([CH3:35])[CH2:32][OH:33])[CH2:27][CH2:28]1)=[O:12])[CH3:2]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21877127N-(4-amino-cyclohexyl)-3-hydroxy-2,2-dimethyl-propionamide hydrochlorideHCID 218771352-[3-(Ethylsulfanyl)phenoxy]-5-fluoronicotinic acid

生成物 1

HCID 178477280HCID 178477280、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-(3-Ethylsulfanyl-phenoxy)-5-fluoro-nicotinic acid (150 mg, 0.51 mmol) was added to a solution of N-(4-amino-cyclohexyl)-3-hydroxy-2,2-dimethyl-propionamide hydrochloride (80:20 cis:trans, 135 mg, 0.54 mmol) and triethylamine (0.21 ml, 1.5 mmol) in dimethylformamide (3 ml) under nitrogen at room temperature. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (108 mg, 0.56 mmol) followed by 1-hydroxybenzotriazole (76 mg, 0.56 mmol) were then added and the reaction was stirred at room temperature for 20 h. The mixture was concentrated under reduced pressure, partitioned between ethyl acetate (20 ml) and water (20 ml) and the organic phase was removed, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on a silica gel eluting with a solvent gradient of dichloromethane:methanol (95:5) and the product was purified by preparative HPLC to give two products.

後処理

  1. additionwere then added
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompartitioned between ethyl acetate (20 ml) and water (20 ml)
  4. customthe organic phase was removed
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on a silica gel eluting with a solvent gradient of dichloromethane:methanol (95:5)
  8. customthe product was purified by preparative HPLC
  9. customto give two products

出典と根拠

ORDレコード
ord-6bf41a25e3d7400ea611bc57bfaeceee
出典データセット
uspto-grants-2006_11
特許番号
US07141586B2

反応ノート

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