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Dibutyltin oxide → Ammonia

HRID 2217906
Notes
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Reaction equation

HRID 2217906 reaction equation
ClC1C=CC2[N:8]=C(C)C=CC=2C=1C(O)=O.[Cl:16][C:17]1[C:18]([NH:34][C:35](=[O:43])[CH2:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[C:22]([N:27]1[CH2:31][CH2:30][C@@H:29]([C:32]#[N:33])[CH2:28]1)[CH:21]=[CH:20]2.C([Sn](=O)CCCC)CCC.[N:54]([Si](C)(C)C)=[N+:55]=[N-:56]>>[NH3:8].[Cl:16][C:17]1[C:18]([NH:34][C:35](=[O:43])[CH2:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[C:22]([N:27]1[CH2:31][CH2:30][C@@H:29]([C:32]3[NH:56][N:55]=[N:54][N:33]=3)[CH2:28]1)[CH:21]=[CH:20]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 11651470HCID 11651470, compoundHCID 68809670N-[6-Chloro-2-[(3R)-3-cyano-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

Product 2

HCID 222AmmoniaHCID 178520228HCID 178520228, compound

Procedure

Prepared according to the method of example 98 (b), using N-[6-chloro-2-[(3R)-3-cyano-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (example 100 (a)) (66 mg), dibutyltin oxide (9 mg) and azidotrimethylsilane (0.06 mL). The residue was purified by ion exchange column (Varian NH2 cartridge, methanol then 3% acetic acid in methanol as eluant). Further purification by ion exchange column (Varian SCX cartridge, methanol then 7N ammonia in methanol as eluant) gave the title compound as a solid (11 mg).

Workup

  1. customPrepared
  2. customThe residue was purified by ion exchange column (Varian NH2 cartridge, methanol
  3. customFurther purification by ion exchange column (Varian SCX cartridge, methanol

Sources & evidence

ORD record
ord-b49aa3d71fd7414fb30c93bad617487f
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07408065B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes