Hydrochloric Acid → HCID 68007944, compound

HRID 526994Notes

Reaction equation

HRID 526994 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15](S(C)=O)[C:14]([F:20])=[CH:13][N:12]=3)=[CH:9][N:8]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:5]2=[N:6][CH:7]=1.[NH2:31][C@H:32]1[CH2:37][CH2:36][CH2:35][C@@H:34]([N:38]2[CH2:42][CH2:41][CH2:40][C:39]2=[O:43])[CH2:33]1.C([O-])([O-])=O.[Na+].[Na+].Cl>C1COCC1.CC#N>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:31][C@H:32]4[CH2:37][CH2:36][CH2:35][C@@H:34]([N:38]5[CH2:42][CH2:41][CH2:40][C:39]5=[O:43])[CH2:33]4)[C:14]([F:20])=[CH:13][N:12]=3)=[CH:9][N:8]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 281688041-((1R,3S)-3-aminocyclohexyl)pyrrolidin-2-one2×HCID 672853215-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

Product 1

HCID 68007944HCID 68007944, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)-pyrrolo[2,3-b]pyridine, 1a, (0.14 g, 0.29 mmol) and 1-((1R,3S)-3-aminocyclohexyl)pyrrolidin-2-one, 45c, (0.10 g, 0.53 mmol) and Na2CO3 (0.09 g, 0.88 mmol) freshly ground, in THF (2.25 mL) and CH3CN (0.45 mL) and heat to 135° C. for 30 min. The mixture was slowly poured into 15 mL 1M HCl and extracted with EtOAc (5×). The combined organic layers were washed with brine, dried over Na2SO4 and filtered and concentrated in vacuo. Flash chromatography (SiO2, 0-20% MeOH—CH2Cl2 gradient) provided the final product as a sticky residue. Trituration with CH3CN provided an off white powder (105 mg) which was impure, but which was taken directly to the final deprotection step.

Workup

  1. extractionextracted with EtOAc (5×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8722588ca944ab2bc5efcf5dd11d02d
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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