Hydrochloric Acid → 1-((1R,3S)-3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)cyclohexyl)pyrrolidin-2-one

HRID 526995Notes

Reaction equation

HRID 526995 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C@@H:20]([N:24]5[CH2:28][CH2:27][CH2:26][C:25]5=[O:29])[CH2:19]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.Cl>CC#N.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C@@H:20]([N:24]5[CH2:28][CH2:27][CH2:26][C:25]5=[O:29])[CH2:19]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68007944HCID 68007944, compound2×

Product 1

HCID 680094471-((1R,3S)-3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)cyclohexyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of partially purified 1-((1R,3S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexyl)pyrrolidin-2-one, 45d, (0.105 g, 0.180 mmol) in CH3CN (5 mL) was treated with HCl (2 mL of 4 M, 8.00 mmol) in dioxane at 70° C. After 2H, the mixture was cooled to room temperature. Then CH3CN was added and the solid that precipitated was triturated with more CH3CN (3×). Preparative HPLC provided the desired product as the HCl salt (35 mg).

Workup

  1. customthe solid that precipitated
  2. customwas triturated with more CH3CN (3×)

Sources & evidence

ORD record
ord-fb1c0e4c65724d11b104c253f08a8835
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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