3-Fluoropyrrolidine → (R)-(1S,3R)-3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)cyclohexyl 3-fluoropyrrolidine-1-carboxylate

HRID 527094Notes

Reaction equation

HRID 527094 reaction equation
[C:1](=O)([O-:44])[O:2][C@@:3]1(N2C(=O)CCC2=O)[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]2[C:15]([F:16])=[CH:14][N:13]=[C:12]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[C:23]([F:26])[CH:24]=4)[N:19]([S:27]([C:30]4[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[CH:18]=3)[N:11]=2)[CH2:4]1.[F:46][C@@H:47]1[CH2:51][CH2:50][NH:49][CH2:48]1>C(#N)C>[F:46][C@@H:47]1[CH2:51][CH2:50][N:49]([C:1]([O:2][C@H:3]2[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]3[C:15]([F:16])=[CH:14][N:13]=[C:12]([C:17]4[C:25]5[C:20](=[N:21][CH:22]=[C:23]([F:26])[CH:24]=5)[N:19]([S:27]([C:30]5[CH:31]=[CH:32][C:33]([CH3:34])=[CH:35][CH:36]=5)(=[O:29])=[O:28])[CH:18]=4)[N:11]=3)[CH2:4]2)=[O:44])[CH2:48]1

Participants

4

Reactant 2

HCID 27591633-FluoropyrrolidineHCID 1317355972,5-dioxopyrrolidin-1-yl((1S,3R)-3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)cyclohexyl) carbonate

Product 1

HCID 68007584(R)-(1S,3R)-3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)cyclohexyl 3-fluoropyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (2,5-dioxopyrrolidin-1-yl) [(1R,3S)-3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]cyclohexyl]carbonate, 75c, (0.125 g, 0.195 mmol) already in acetonitrile was added (3R)-3-fluoropyrrolidine (0.445 g, 4.991 mmol) and the reaction mixture was stirred at room temperature for 20 hours; The reaction was monitored by HPLC until no more starting material was remaining. The reaction mixture was concentrated in vacuo and was carried on into the next reaction without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customwas carried on into the next reaction without further purification

Sources & evidence

ORD record
ord-060571221991484989e560fc66de9e00
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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