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

HRID 131470Notes

Reaction equation

HRID 131470 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][CH2:23][O:24][CH3:25])[CH2:16]3)[C:12]3[CH:11]=[CH:10][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+]>ClCCl>[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][CH2:23][O:24][CH3:25])[CH2:16]3)[C:12]3[CH:11]=[CH:10][S:9][C:8]=3[NH:7][C:6]=2[CH:26]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 9999487(S)-6-Fluoro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene

Product 1

HCID 58625881(S)-6-Fluoro-10-[3-(3-methoxy-propyl)-4-methyl-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azuleneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine (S)-6-fluoro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene (220.1 mg, 0.59 mmol), formaldehyde (52.5 μL, 0.64 mmol, 37% in water), and dichloromethane (8.0 ml). Stir the mixture at ambient temperature for 5 minutes and then add sodium triacetoxyborohydride (186.8 mg, 6.88 mmol). After stirring for 30 minutes at ambient temperature, quench the reaction with saturated sodium bicarbonate. Remove the organic portion and wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (90:10) to give 195.1 mg (86%) of the title compound: mass spectrum (ion spray): m/z=389.1 (M+1).

Workup

  1. stirringAfter stirring for 30 minutes at ambient temperature
  2. customquench
  3. customthe reaction with saturated sodium bicarbonate
  4. customRemove the organic portion
  5. washwash (brine)
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (90:10)

Sources & evidence

ORD record
ord-bad6b59c01b74f76b5398eae835a9aab
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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