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1,2-Dichloroethane → (S)-6-Fluoro-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene hydrochloride

HRID 131471
Notes
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Reaction equation

HRID 131471 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH2:21][CH2:22][O:23][CH3:24])[CH2:16]3)[C:12]3[CH:11]=[C:10]([CH3:25])[S:9][C:8]=3[NH:7][C:6]=2[CH:26]=1.C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].[Cl:48]CCCl>>[ClH:48].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH3:29])[C@@H:17]([CH2:21][CH2:22][O:23][CH3:24])[CH2:16]3)[C:12]3[CH:11]=[C:10]([CH3:25])[S:9][C:8]=3[NH:7][C:6]=2[CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10317297HCID 10317297, compound

Product 1

HCID 69213939(S)-6-Fluoro-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene hydrochloride
Yield 100%

Conditions

Temperature
17.5 °C

Procedure

Stir (S)-6-fluoro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (5.00 g, 13.4 mmol) under nitrogen to dissolve in 1,2-dichloroethane (DCE, 55 mL). Cool to 15-20° C. and add formaldehyde (37% wt. in water, 1.03 g solution, 0.38 g, 12.7 mmol) in one portion. Add sodium triacetoxyborohydride (3.41 g, 16.1 mmol) in portions over 5-10 minutes, keeping the pot temperature below 20° C. Stir at 15-20° C. for 15 minutes, and then allow warming to ambient temperature. Stir for 2 hours, and then add aqueous saturated sodium bicarbonate (50 mL). Stir for 15 minutes, and then separate layers. Extract the product with methylene chloride. Extract the combined organic layers with brine, dry over magnesium sulfate, and then concentrate under reduced pressure to a residue. Add methylene chloride to the residue and concentrate under reduced pressure to give 4.94 g (100%) of the free base of the title compound. 1H NMR (400 MHz, DMSO-d6) 87.78 (bs, 1H), 6.79 (m, 1H), 6.68 (m, 1H), 6.53 (m, 1H), 6.34 (s, 1H), 3.74 (m, 2H), 3.36 (m, 3H), 3.22 (s, 3H), 2.95 (m, 1H), 2.77 (m, 1H), 2.69 (m, 1H), 2.30 (s, 3H), 2.23 (s, 3H), 2.17 (bs, 1H), 1.84 (m, 1H), 1.52 (m, 1H). HRMS (ES) exact mass M+H calcd for C20H25FN4OS 389.1811; found 389.1802.

Workup

  1. customthe pot temperature below 20° C
  2. temperatureallow warming to ambient temperature
  3. stirringStir for 2 hours
  4. stirringStir for 15 minutes
  5. extractionExtract the product with methylene chloride
  6. extractionExtract the combined organic layers with brine
  7. dry with materialdry over magnesium sulfate
  8. concentrationconcentrate under reduced pressure to a residue
  9. concentrationAdd methylene chloride to the residue and concentrate under reduced pressure

Sources & evidence

ORD record
ord-2fe288e10c7c4c22831e93ef89b08f1d
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384934B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes