Acetic Acid → HCID 10387898, compound

HRID 271698Notes

Reaction equation

HRID 271698 reaction equation
C=O.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]4[S:30][C:29]5[CH2:28][CH2:27][NH:26][CH2:25][CH2:24][C:23]=5[C:22]=4[CH:31]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.[BH3-][C:33]#N.[Na+].C(O)(=O)C.[OH-].[Na+]>O.C(#N)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]4[S:30][C:29]5[CH2:28][CH2:27][N:26]([CH3:33])[CH2:25][CH2:24][C:23]=5[C:22]=4[CH:31]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 9979213HCID 9979213, compound

Product 1

HCID 10387898HCID 10387898, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

0.18 mL (2.41 mmol) 37% formalin solution in water are added to a solution of 100 mg (0.24 mmol) 3-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-6,7,8,9-tetrahydro-5H-10-thia-7-aza-benzo[a]azulene (see 3.60f) in 5 mL acetonitrile. Then 60 mg (0.96 mmol) NaBH3CN and 56 μL (0.96 mmol) acetic acid are added and the reaction mixture is stirred overnight. The solution is combined with 2 M NaOH and extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography by HPLC-MS.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe purification

Sources & evidence

ORD record
ord-b2eb988bb32d4e9d8d0957bebec658df
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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