Formaldehyde → HCID 136005618, compound

HRID 1350529Notes

Reaction equation

HRID 1350529 reaction equation
C=O.[CH:3]([C:6]1[S:15][C:14]2[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=[C:9]([N:20]3[CH2:25][CH2:24][NH:23][C@@H:22]([CH2:26][C@@H:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[OH:28])[CH2:21]3)[C:8]=2[N:7]=1)([CH3:5])[CH3:4].[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(=O)(O)[O-].[Na+]>[CH:3]([C:6]1[S:15][C:14]2[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=[C:9]([N:20]3[CH2:25][CH2:24][N:23]([CH3:35])[C@@H:22]([CH2:26][C@@H:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[OH:28])[CH2:21]3)[C:8]=2[N:7]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136005608HCID 136005608, compound

Product 1

HCID 136005618HCID 136005618, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Add formaldehyde (23 μL, 0.29 mmol, 37% in water) to a solution of (S,S)-2-[4-(2-isopropyl-4H-3-thia-1,4,9-triaza-benzo[f]azulen-10-yl)-piperazin-2-yl]-1-phenyl-ethanol (117 mg, 0.26 mmol) in dichloroethane (5 mL). Stir 15 min at ambient temperature. Add sodium triacetoxyborohydride (83 mg, 0.39 mmol) and stir 2 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%–4%) as the eluent to give 68 mg (56%) of the title compound: mass spectrum (ion spray): m/z=462 (M+1), 460 (M−1). HR-MS calculated for C26H32N5OS: 462.2328. Found 462.2322. 1H NMR (DMSO-d6): δ 7.82 (s, 1H), 7.35–7.18 (m, 5H), 6.91–6.76 (m, 3H), 6.69 (br d, 1H), 5.29 (s, 1H), 4.58–4.46 (m, 1H), 4.14–3.77 (m, 2H), 3.02–3.17 (m, 2), 2.90 (dd, 1H), 2.74–2.65 (m, 1H), 2.28–2.11 (m, 1H), 2.14 (s, 3H), 2.03–1.84 (m, 2H) 1.70–1.54 (m, 1H), 1.26 (d, 6H).

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-2a98e7a8e52548ab94242b0ec5fc4062
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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