Formaldehyde → HCID 136005587, compound

HRID 1350424Notes

Reaction equation

HRID 1350424 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C@@H:11]1[NH:16][CH2:15][CH2:14][N:13]([C:17]2[C:26]3[CH:25]=[C:24]([CH3:27])[S:23][C:22]=3[NH:21][C:20]3[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=3[N:18]=2)[CH2:12]1.C=O.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C@@H:11]1[N:16]([CH3:34])[CH2:15][CH2:14][N:13]([C:17]2[C:26]3[CH:25]=[C:24]([CH3:27])[S:23][C:22]=3[NH:21][C:20]3[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=3[N:18]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136005593HCID 136005593, compound

Product 1

HCID 136005587HCID 136005587, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Combine 10-((S)-3-[2-(2,4-difluoro-phenyl)-ethyl]-piperazin-1-yl)-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (57.3 mg, 0.61 mmol), formaldehyde (11.7 μL, 0.14 mmol, 37% in water), and 1,2-dichloroethane (5.0 ml). Stir the mixture at ambient temperature for 5 minutes and then add sodium triacetoxyborohydride (41.5 mg, 0.20 mmol). After stirring for 30 minutes at ambient temperature, quench the reaction with saturated sodium bicarbonate. Remove the organic portion, extract the aqueous with dichloromethane and combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue to give 54.4 mg (92%) of the title compound: mass spectrum (ion spray): m/z=452.9 (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. extractionextract the aqueous with dichloromethane and combine
  6. washwash (brine)
  7. dry with materialdry (sodium sulfate)

Sources & evidence

ORD record
ord-2699b113c8ca4f42aa61085e3839f252
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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