Trifluoroacetic acid → (S)-1-[(S)-2-((S)-2-methylamino-propionylamino)-2-(tetrahydro-pyran-4-yl)-acetyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-fluoro-6-methyl-phenyl)-amide

HRID 627060ノート

反応式

HRID 627060 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([C@H:12]1[N:20]([C:21](=[O:43])[C@@H:22]([NH:29][C:30](=[O:42])[C@@H:31]([N:33](C)[C:34](=O)OC(C)(C)C)[CH3:32])[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([C@H:12]1[N:20]([C:21](=[O:43])[C@@H:22]([NH:29][C:30](=[O:42])[C@@H:31]([NH:33][CH3:34])[CH3:32])[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 131735274tert-butyl (S)-1-((S)-2-((S)-2-(2-fluoro-6-methylphenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethylamino)-1-oxopropan-2-yl(methyl)carbamate

生成物 1

HCID 73603260(S)-1-[(S)-2-((S)-2-methylamino-propionylamino)-2-(tetrahydro-pyran-4-yl)-acetyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-fluoro-6-methyl-phenyl)-amide収率 52%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 50 mL round-bottomed flask, tert-butyl (S)-1-((S)-2-((S)-2-(2-fluoro-6-methylphenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethylamino)-1-oxopropan-2-yl(methyl)carbamate (30 mg, 50.2 μmol, Eq: 1.00) was combined with DCM (3 mL) to give a colorless solution. TFA (1 mL, 13.0 mmol, Eq: 259) was added and the reaction was stirred at rt for 30 min. The reaction mixture was concentrated in vacuo and the residue was treated with saturated aqueous NaHCO3 (10 mL). The resulting mixture was extracted with DCM (2×10 mL), the combined organic layers dried over Na2SO4, and then concentrated in vacuo to give (S)-1-[(S)-2-((S)-2-methylamino-propionylamino)-2-(tetrahydro-pyran-4-yl)-acetyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-fluoro-6-methyl-phenyl)-amide (13 mg), m/z=498 (M+H).

後処理

  1. customto give a colorless solution
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue was treated with saturated aqueous NaHCO3 (10 mL)
  4. extractionThe resulting mixture was extracted with DCM (2×10 mL)
  5. dry with materialthe combined organic layers dried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-82009efba00e40f8b7764b75682825b3
出典データセット
uspto-grants-2016_04
特許番号
US09309248B2

反応ノート

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