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4-Pyridinemethanamine → (S)-Methyl 2-(4-chloro-8-oxo-9-(pyridin-4-ylmethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetate

HRID 132178
Notes
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Reaction equation

HRID 132178 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][C@@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17]C)=O)[C:5]([CH2:11]Cl)=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][N:24]([CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[C:15](=[O:17])[C@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:13][C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 773174-PyridinemethanamineHCID 59731905(S)-Dimethyl 2-((7-chloro-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinate

Product 1

HCID 59731975(S)-Methyl 2-(4-chloro-8-oxo-9-(pyridin-4-ylmethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetateYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent
2×

Procedure

(S)-Dimethyl 2-((7-chloro-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinate (120 mg, 0.33 mmol) was dissolved in DMF (1.0 mL). 4-Aminomethylpyridine (100 μL, 1.0 mmol) was added to the mixture. Reaction stirred at room temperature for 24 hours. Mixture was diluted with ethyl acetate. Mixture was washed twice with water and once with brine. Organic was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was dissolved in toluene (4 mL). Acetic acid (1 mL) was added to the mixture. Reaction was heated at reflux for 3.5 hours. Mixture was cooled to room temperature then diluted with ethyl acetate. Material was washed once with water and twice with aqueous sodium bicarbonate. Aqueous was made basic with sodium bicarbonate. Back extracted from the aqueous twice with ethyl acetate. Combined organics were dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was purified with silica gel chromatography eluting dichloromethane and 2N ammonia in methanol. Title compound was obtained as yellow solid in 48% yield.

Workup

  1. customReaction
  2. washMixture was washed twice with water and once with brine
  3. dry with materialOrganic was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionResidue was dissolved in toluene (4 mL)
  7. additionAcetic acid (1 mL) was added to the mixture
  8. customReaction
  9. temperaturewas heated
  10. temperatureat reflux for 3.5 hours
  11. temperatureMixture was cooled to room temperature
  12. washMaterial was washed once with water and twice with aqueous sodium bicarbonate
  13. extractionBack extracted from the aqueous twice with ethyl acetate
  14. dry with materialCombined organics were dried (magnesium sulfate)
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo
  17. customResidue was purified with silica gel chromatography
  18. washeluting dichloromethane and 2N ammonia in methanol

Sources & evidence

ORD record
ord-3ed04bff3d1249cf82994da609133364
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384930B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes