Formaldehyde → HCID 135797768, compound

HRID 1350433Notes

Reaction equation

HRID 1350433 reaction equation
C=O.[CH3:3][C:4]1[S:13][C:12]2[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[N:8]=[C:7]([N:18]3[CH2:23][CH2:22][NH:21][C@@H:20]([CH2:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH:27]=4)[CH2:19]3)[C:6]=2[CH:5]=1.[C:36](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:3][C:4]1[S:13][C:12]2[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[N:8]=[C:7]([N:18]3[CH2:23][CH2:22][N:21]([CH3:36])[C@@H:20]([CH2:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH:27]=4)[CH2:19]3)[C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136005594HCID 136005594, compound

Product 1

HCID 135797768HCID 135797768, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Add formaldehyde (101 μL, 1.28 mmol, 37% in water) to a solution of (S)-2-methyl-10-[3-(2-naphthalen-2-yl-ethyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene (525 mg, 1.16 mmol) in methylene chloride (20 mL). Stir 15 min at ambient temperature. Add sodium triacetoxyborohydride (369 mg, 1.7 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 silica gel chromatography using 2N ammonia in methanol-methylene chloride (2.5%) as the eluent to give 550 mg (100%) of the title compound: mass spectrum (ion spray): m/z=467 (M+1), 465 (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 5.7 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 silica gel chromatography

Sources & evidence

ORD record
ord-c80e0bfadf014581af4dcf8da24a7243
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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