benzyl (S)-1-((S)-1-((S)-2-(2,6-difluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(2-(methylsulfonyl)ethyl)carbamate → (S)-1-{(S)-2-[(S)-2-(2-methanesulfonyl-ethylamino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2,6-difluoro-phenyl)-amide

HRID 627049Notes

Reaction equation

HRID 627049 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]([C@H:12]1[N:20]([C:21](=[O:48])[C@@H:22]([NH:26][C:27](=[O:47])[C@@H:28]([N:30]([CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44])C(=O)OCC2C=CC=CC=2)[CH3:29])[CH:23]([CH3:25])[CH3:24])[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11]>[Pd].CO>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[NH:9][C:10]([C@H:12]1[N:20]([C:21](=[O:48])[C@@H:22]([NH:26][C:27](=[O:47])[C@@H:28]([NH:30][CH2:41][CH2:42][S:43]([CH3:46])(=[O:44])=[O:45])[CH3:29])[CH:23]([CH3:24])[CH3:25])[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11]

Participants

4

Reactant 1

HCID 131735267benzyl (S)-1-((S)-1-((S)-2-(2,6-difluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(2-(methylsulfonyl)ethyl)carbamate

Product 1

HCID 73603309(S)-1-{(S)-2-[(S)-2-(2-methanesulfonyl-ethylamino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2,6-difluoro-phenyl)-amideYield 67.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 100 mL round-bottomed flask, benzyl (S)-1-((S)-1-((S)-2-(2,6-difluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(2-(methylsulfonyl)ethyl)carbamate (33 mg, 48.1 μmol, Eq: 1.00) and 10% palladium on carbon (5.12 mg, 4.81 μmol, Eq: 0.1) were combined with MeOH (5 mL) to give a black suspension which was stirred under a hydrogen atmosphere (balloon) at rt for 1 h. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo to give (S)-1-{(S)-2-[(S)-2-(2-methanesulfonyl-ethylamino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2,6-difluoro-phenyl)-amide (18 mg), m/z=552 (M+H).

Workup

  1. customto give a black suspension which
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-657ea04ccf41480098248e7f73fcddb4
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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