1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-benzyl-3-(3,4-dihydroxypyrrolidin-1-yl)-2-(S)-hydroxy-3-oxopropyl]amide

HRID 1693460ノート

反応式

HRID 1693460 の反応式
[OH:1][C@H:2]1[C@@H:6]([OH:7])[CH2:5][NH:4][CH2:3]1.[Cl:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18]([NH:20][C@@H:21]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:22]([OH:26])[C:23](O)=[O:24])=[O:19])[NH:15][C:12]2=[CH:13][N:14]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.[Cl-].[Na+].O>[CH2:27]([C@H:21]([NH:20][C:18]([C:16]1[NH:15][C:12]2=[CH:13][N:14]=[C:9]([Cl:8])[CH:10]=[C:11]2[CH:17]=1)=[O:19])[C@H:22]([OH:26])[C:23]([N:4]1[CH2:5][CH:6]([OH:7])[CH:2]([OH:1])[CH2:3]1)=[O:24])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 111879523-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acidHCID 13329882(3R,4S)-pyrrolidine-3,4-diol

生成物 1

HCID 866017675-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-benzyl-3-(3,4-dihydroxypyrrolidin-1-yl)-2-(S)-hydroxy-3-oxopropyl]amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

cis-3,4-Dihydroxypyrrolidine (Preparation 23, 9 mg, 0.087 mmol) was added to a solution of 3-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid (EXAMPLE 124, 30 mg, 0.080 mmol), HOBt (14 mg, 0.091 mmol), DIPEA (31 μL, 0.18 mmol) and EDCI (18 mg, 0.094 mmol) in DMF (3 mL). After stirring for 12 h the mixture was added to diluted brine (100 mL, water/brine: 1/1). Extraction with ethyl acetate (4×25 mL), washing of the combined extracts with brine (50 mL) and drying (MgSO4) gave, after concentration, a residue which was purified by preparative LCMS to give the title compound as a colourless solid. m/z (ES+)=459.29 [M+H]+; RT=2.87 min.

後処理

  1. extractionExtraction with ethyl acetate (4×25 mL)
  2. washwashing of the combined extracts with brine (50 mL)
  3. dry with materialdrying (MgSO4)
  4. customgave
  5. concentrationafter concentration
  6. customa residue which was purified by preparative LCMS

出典と根拠

ORDレコード
ord-0d66f6be66344f72a1152391701640b8
出典データセット
uspto-grants-2012_04
特許番号
US08158622B2

反応ノート

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