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 1693464ノート

反応式

HRID 1693464 の反応式
[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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2a8069eb17ff47a587eab2259087d226
出典データセット
uspto-grants-2012_04
特許番号
US08158622B2

反応ノート

読み込み中…