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Formaldehyde → (S)-7-Chloro-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131479
Notes
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Reaction equation

HRID 131479 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[S:8][C:9]([CH3:24])=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH2:21][O:22][CH3:23])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1.C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[S:8][C:9]([CH3:24])=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:29])[C@@H:16]([CH2:20][CH2:21][O:22][CH3:23])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 136090361(S)-7-Chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Product 1

HCID 136090349(S)-7-Chloro-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Combine (S)-7-chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (33.3 g, 85.2 mmol) and 1,2-dichloroethane (DCE, 500 mL). Add formaldehyde (37% wt. in water, 6.91 g solution, 2.56 g, 85.2 mmol) in one portion and stir at ambient temperature for 5 minutes. Add sodium triacetoxyborohydride (3.41 g, 16.1 mmol) in portions over 5-10 minutes, keeping the pot temperature below 25° C. Stir at ambient temperature overnight. Add saturated aqueous sodium bicarbonate (333 mL). Stir for 15 minutes, and then separate layers. Extract the aqueous layer with methylene chloride (250 mL). Wash the combined organic layers with water (3×333 mL), dry over sodium sulfate, and then concentrate ins vacuo to a residue (>100% recovery). Purify the residue by flash column chromatography, eluting with (100% CH2Cl2 to 93/7 CH2Cl2/MeOH) 91.2% recovery of the title compound. 1H NMR (500 MHz, DMSO-d6) δ 1.49 (m, 1H), 1.82 (m, 1H), 2.13 (m, 2H), 2.20 (s, 3H), 2.27 (s, 3H), 2.74 (m, 2H), 2.98 (bt, 1H), 3.19 (s, 3H), 3.32 (m, 2H), 3.77 (bm, 2H).

Workup

  1. customthe pot temperature below 25° C
  2. stirringStir for 15 minutes
  3. extractionExtract the aqueous layer with methylene chloride (250 mL)
  4. washWash the combined organic layers with water (3×333 mL)
  5. dry with materialdry over sodium sulfate
  6. customPurify the residue by flash column chromatography
  7. washeluting with (100% CH2Cl2 to 93/7 CH2Cl2/MeOH) 91.2% recovery of the title compound

Sources & evidence

ORD record
ord-2d93fa670c69445d8df8e60c68c6b094
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384934B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes