Sodium Hydroxide → HCID 68295992, compound

HRID 589958Notes

Reaction equation

HRID 589958 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[OH:13][S:14](Cl)(=[O:16])=O.P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:24]1[C:26]2([CH2:31][N:30]([C:32]3[C:33]4[CH:40]=[CH:39][NH:38][C:34]=4[N:35]=[CH:36][N:37]=3)[CH2:29][CH2:28][NH:27]2)[CH2:25]1>C(Cl)Cl.N1C=CC=CC=1>[CH2:2]([O:9][NH:10][S:14]([N:27]1[C:26]2([CH2:24][CH2:25]2)[CH2:31][N:30]([C:32]2[C:33]3[CH:40]=[CH:39][NH:38][C:34]=3[N:35]=[CH:36][N:37]=2)[CH2:29][CH2:28]1)(=[O:16])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 102312Benzyloxyamine hydrochlorideHCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine2×

Product 1

HCID 68295992HCID 68295992, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

O-benzylhydroxylamine hydrochloride (5.13 mmol) was dissolved in DCM (20 mL) and treated with 1N NaOH (6 mL). The phases were separated and the organic phase was washed with H2O, dried for 30 min using Na2SO4 and filtered. The obtained solution was cooled to 0° C. and slowly added a solution of HOSO2Cl (1.71 mmol) in dry DCM (5 mL). After 1 h at 0° C. a white precipitate was filtered off. The precipitate was washed with DCM and thereafter Et2O before being dried (freezedryer). The obtained dry compound was suspended in dry toluene (15 mL), added PCl5 (2.05 mmol) and stirred at reflux for 1 h. After being cooled to rt, the reaction mixture was filtered and the filtrate was concentrated in vacuo. The obtained oil was added neat to a solution of 4-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 21) (1.71 mmol) in pyridine (7 mL) and stirred at 40° C. for 16 h. The pure compound was obtained by standard preparative HPLC purification.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with H2O
  3. customdried for 30 min
  4. filtrationfiltered
  5. filtrationAfter 1 h at 0° C. a white precipitate was filtered off
  6. washThe precipitate was washed with DCM
  7. dry with materialEt2O before being dried (freezedryer)
  8. temperatureat reflux for 1 h
  9. temperatureAfter being cooled to rt
  10. filtrationthe reaction mixture was filtered
  11. concentrationthe filtrate was concentrated in vacuo
  12. stirringstirred at 40° C. for 16 h
  13. customThe pure compound was obtained by standard preparative HPLC purification

Sources & evidence

ORD record
ord-c031b77f6d4c4dfa9d4ca10b9151acd5
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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