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Sodium Methoxide → (7S)-7-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-2-azaspiro[4.5]decan-3-one

HRID 75013
Notes
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Reaction equation

HRID 75013 reaction equation
ClC1N=C(N[C@H]2CCCC3(CNC(=O)C3)C2)C(F)=CN=1.[Cl:21][C:22]1[CH:23]=[C:24]2[C:30]([C:31]3[N:36]=[C:35]([NH:37][C@H:38]4[CH2:48][CH2:47][CH2:46][C:40]5([CH2:44][NH:43][C:42](=[O:45])[CH2:41]5)[CH2:39]4)[C:34]([F:49])=[CH:33][N:32]=3)=[CH:29][N:28](S(C3C=CC(C)=CC=3)(=O)=O)[C:25]2=[N:26][CH:27]=1.C[O-].[Na+]>CO>[Cl:21][C:22]1[CH:23]=[C:24]2[C:30]([C:31]3[N:36]=[C:35]([NH:37][C@H:38]4[CH2:48][CH2:47][CH2:46][C:40]5([CH2:44][NH:43][C:42](=[O:45])[CH2:41]5)[CH2:39]4)[C:34]([F:49])=[CH:33][N:32]=3)=[CH:29][NH:28][C:25]2=[N:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 68007747(7S)-7-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-2-azaspiro[4.5]decan-3-oneHCID 86667444(7S)-7-(2-chloro-5-fluoropyrimidin-4-ylamino)-2-azaspiro[4.5]decan-3-one

Product 1

HCID 68007993(7S)-7-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-2-azaspiro[4.5]decan-3-oneYield 75.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (7S)-7-(2-chloro-5-fluoropyrimidin-4-ylamino)-2-azaspiro[4.5]decan-3-one, 62d, (0.091 g, 0.159 mmol) in MeOH (2 mL) was added NaOMe (2 mL of 25% w/v, 9.255 mmol). The reaction was stirred for 0.5 hours then concentrated in vacuo. The material was purified by reverse phase HPLC (Water/HCl:MeOH) to give a mixture of diastereomers. The fractions containing pure product were combined and concentrated to give 50 mg of the HCl salt of 969.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe material was purified by reverse phase HPLC (Water/HCl:MeOH)
  3. customto give
  4. additiona mixture of diastereomers
  5. additionThe fractions containing pure product
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7ddc895212514a20b58ca2c7f11609ad
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829007B2

Reaction notes

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