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

HRID 1693421노트

반응식

HRID 1693421 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][C@@H:14]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:15]([OH:19])[C:16](O)=[O:17])=[O:12])[NH:8][C:5]2=[CH:6][N:7]=1.[OH:27][C@H:28]1[C@@H:32]([OH:33])[CH2:31][NH:30][CH2:29]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[CH2:20]([C@H:14]([NH:13][C:11]([C:9]1[NH:8][C:5]2=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:10]=1)=[O:12])[C@@H:15]([OH:19])[C:16]([N:30]1[CH2:31][C@H:32]([OH:33])[C@H:28]([OH:27])[CH2:29]1)=[O:17])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13329882(3R,4S)-pyrrolidine-3,4-diolHCID 59753553(S)-3-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-(R)-2-hydroxy-4-phenylbutyric acid

생성물 1

HCID 113401055-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-benzyl-3-(cis-3,4-dihydroxypyrrolidine-1-yl)-2(R)-hydroxy-3-oxopropyl]amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (S)-3-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(R)-hydroxy-4-phenylbutyric acid (EXAMPLE 44, 50 mg, 0.13 mmol), cis-3,4-dihydroxypyrrolidine (Preparation 23, 15 mg, 0.15 mmol) and HOBt (27 mg, 0.20 mmol) in DMF (5 mL), was added DIPEA (47 μL, 0.27 mmol). After stirring for 5 min, EDCI (28 mg, 0.15 mmol) was added and the reaction stirred at rt for 72 h. The solvent was removed in vacuo and the residue partitioned between water (30 mL) and ethyl acetate (3×30 mL). The combined organic fractions were dried (MgSO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with methanol/dichloromethane (1:9) to give the title compound as a white solid. m/z (ES+)=459 [M+H]+. RT=3.07 min.

후처리

  1. stirringthe reaction stirred at rt for 72 h
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between water (30 mL) and ethyl acetate (3×30 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by chromatography on silica gel eluting with methanol/dichloromethane (1:9)

출처 및 근거

ORD 기록
ord-c21f9a0c913346d791adf277e73f09e7
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158622B2

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