Formaldehyde → HCID 136005548, compound

HRID 1350437Notes

Reaction equation

HRID 1350437 reaction equation
C=O.[O:3]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@@H:10]2[NH:15][CH2:14][CH2:13][N:12]([C:16]3[C:25]4[CH:24]=[C:23]([CH3:26])[S:22][C:21]=4[NH:20][C:19]4[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=4[N:17]=3)[CH2:11]2)=[CH:4]1.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[O:3]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@@H:10]2[N:15]([CH3:31])[CH2:14][CH2:13][N:12]([C:16]3[C:25]4[CH:24]=[C:23]([CH3:26])[S:22][C:21]=4[NH:20][C:19]4[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=4[N:17]=3)[CH2:11]2)=[CH:4]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 135932168HCID 135932168, compound

Product 1

HCID 136005548HCID 136005548, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Add formaldehyde (49 μL, 0.61 mmol, 37% in water) to a solution of (S)-10-[3-(2-furan-3-yl-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (219 mg, 0.56 mmol) in methylene chloride (20 mL). Stir 15 min at ambient temperature. Add sodium triacetoxyborohydride (177 mg, 0.56 mmol) and stir 1 h at ambient temperature. Dilute with saturated sodium bicarbonate solution and extract with methylene chloride. Dry the extracts with sodium sulfate, filter and concentrate the filtrate. Purify by radial silica gel chromatography using a 2 mm plate and 2N ammonia in methanol-methylene chloride (1%–2.5%) as the eluent to give 179 mg (79%) of the title compound: mass spectrum (ion spray): m/z=407 (M+1), 405 (M−1). HPLC: Symmetry C18 column (3.5 μm, 4.6×50 mm). Gradient 5% to 90% solvent B in 7 min. Solvent A was 0.1% (v/v) TFA in water and solvent B was acetonitrile. Retention time 5.4 min; 100% pure;

Workup

  1. extractionextract with methylene chloride
  2. dry with materialDry the extracts with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate the filtrate
  5. customPurify by radial silica gel chromatography

Sources & evidence

ORD record
ord-05db4ecdd5134075808f478c29d5a5bf
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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