Hydrochloric Acid → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(4-methylaminopiperidin-1-yl)-2-oxoethyl]amide

HRID 1693464노트

반응식

HRID 1693464 반응식
[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][C@H:7]([NH:30][C:31]([C:33]2[NH:42][C:36]3=[CH:37][N:38]=[C:39]([Cl:41])[CH:40]=[C:35]3[CH:34]=2)=[O:32])[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]([CH3:29])S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C1C=CC(S)=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@H:7]([NH:30][C:31]([C:33]2[NH:42][C:36]3=[CH:37][N:38]=[C:39]([Cl:41])[CH:40]=[C:35]3[CH:34]=2)=[O:32])[C:8]([N:10]2[CH2:11][CH2:12][CH:13]([NH:16][CH3:29])[CH2:14][CH2:15]2)=[O:9])=[CH:43][CH:44]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 597537125-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-(4-fluorobenzyl)-2-{4-[methyl(2-nitrobenzenesulfonyl)amino]piperidin-1-yl}-2-oxoethyl)amide

생성물 1

HCID 597535225-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(4-methylaminopiperidin-1-yl)-2-oxoethyl]amide

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-(4-fluorobenzyl)-2-{4-[methyl-(2-nitrobenzenesulfonyl)amino]piperidin-1-yl}-2-oxoethyl)amide (Preparation 76, 82 mg, 0.13 mmol) in acetonitrile (6 mL) was added phenylthiol (145 μL, 1.4 mmol) followed by potassium carbonate (230 mg, 1.66 mmol) and the reaction heated to 50° C. for 24 h. To the mixture was added diethyl ether (10 mL) and 1M HCl (15 mL) and stirred for 5 min. The organic layer was separated and washed with 1M HCl (15 mL) before combining the aqueous layers. The solution was basified to pH9 with solid potassium carbonate and extracted with ethyl acetate (2×20 mL). Organic layers were combined, washed with brine (2×20 mL) and dried (MgSO4). Removal of the solvent in vacuo provided the desired product as an off-white powder. m/z (ES+)=458.40 [M+H]+; RT=2.67 min. A small portion of the product (10 mg) was dissolved in methanol (2 mL) and 1M HCl added to bring the solution to pH 1-2. After stirring for 20 min the solvent was removed in vacuo to give the title compound as the hydrochloride salt as a yellow powder. m/z (ES+)=458.38 [M+H]+; RT=2.64 min.

후처리

  1. customThe organic layer was separated
  2. washwashed with 1M HCl (15 mL)
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washwashed with brine (2×20 mL)
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent in vacuo

출처 및 근거

ORD 기록
ord-2a8069eb17ff47a587eab2259087d226
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158622B2

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