Ammonium Hydroxide → HCID 58550623, compound

HRID 1890710Notes

Reaction equation

HRID 1890710 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:34][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([C:30](NN)=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2.[NH4+].[OH-]>C(Cl)Cl.O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:34][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([CH:30]=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 58550577HCID 58550577, compound

Product 1

HCID 58550623HCID 58550623, compound

Reagents, catalysts & solvents 3

HCID 178511488HCID 178511488, compoundCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a rapidly stirred solution of (2S)-2′-oxo-1′-{[2-(trimethylsilyl)eth-oxy]methyl}-1,1′,2′,3-tetrahydrospiro[cyclopenta[b]quinoline-2,3′-pyrrolo[2,3-b]pyridine]-7-carbohydrazide from Step H (317 mg, 0.667 mmol) in DCM (6.8 mL) was added water (2.7 mL) plus concentrated aqueous NH4OH (0.6 mL) and lastly potassium ferricyanide (549 mg, 1.67 mmol). After 4.5 hours the reaction was diluted with water (20 mL) and DCM (40 mL). The aqueous layer was extracted once with DCM (20 mL). The combined organics were washed successively with water then half-saturated brine and then dried over sodium sulfate. The organics were then filtered, concentrated in vacuo, and applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—99:1 to 90:10. Clean product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=446 (M+1).

Workup

  1. extractionThe aqueous layer was extracted once with DCM (20 mL)
  2. washThe combined organics were washed successively with water
  3. dry with materialhalf-saturated brine and then dried over sodium sulfate
  4. filtrationThe organics were then filtered
  5. concentrationconcentrated in vacuo
  6. customapplied to a silica gel column for purification
  7. washeluting with a gradient of CH2Cl2
  8. additionClean product-containing fractions
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fac5351aa7804aa2bbc8b30e6fc12639
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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