Formaldehyde → HCID 136360201, compound

HRID 1350390Notes

Reaction equation

HRID 1350390 reaction equation
[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]=[C:5]([N:16]3[CH2:21][CH2:20][NH:19][C@@H:18]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:17]3)[C:4]=2[CH:3]=1.C=O.[CH2:32](Cl)[Cl:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)(O)[O-].[Na+]>[ClH:33].[ClH:33].[ClH:33].[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]=[C:5]([N:16]3[CH2:21][CH2:20][N:19]([CH3:32])[C@@H:18]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:17]3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 135932137HCID 135932137, compound

Product 1

HCID 136360201HCID 136360201, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Combine 2-methyl-10-((S)-3-(2-pyridin-2-yl-ethyl)-piperazin-1-yl)-4H-3-thia-4,9-diaza-benzo[f]azulene (200 mg, 0.50 mmol) and formaldehyde (43 μL, 0.54 mmol, 37% in water), and methylene chloride (5 mL). Stir 10 minutes at ambient temperature. Add sodium triacetoxyborohydride (158 mg, 0.74 mmol) and stir 1 hour 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 (0%–4%) as the eluent to give the free base. Crystallize as the trihydrochloride salt from ethyl acetate and ethanol to give the title compound (161 mg, 78%): Mass spectrum (ion spray): m/z=418 (M+1), 416 (M−1). Analysis calculated for C24H27N5S.3HCl: C, 54.70; H, 5.74; N, 13.29. Found: C, 54.88; H, 6.02; N, 12.96.

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
  6. customto give the free base
  7. customCrystallize as the trihydrochloride salt from ethyl acetate and ethanol

Sources & evidence

ORD record
ord-7430d30e17924e69aef14d6b649d9134
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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