Formaldehyde → HCID 59513604, compound

HRID 1159834Notes

Reaction equation

HRID 1159834 reaction equation
[CH2:1]=O.[CH2:3]([NH:5][CH3:6])[CH3:4].[F:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][N:14]2[S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:10][C:9]=1[OH:26]>CCO>[CH2:3]([N:5]([CH2:1][C:10]1[C:9]([OH:26])=[C:8]([F:7])[CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][N:14]2[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 12219N-MethylethylamineHCID 67241531HCID 67241531, compound2×

Product 1

HCID 59513604HCID 59513604, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Paraformaldehyde (20.6 mg, 0.686 mmol) and N-ethylmethylamine (0.059 ml, 0.686 mmol) in EtOH (1 ml) was heated until a clear solution was obtained. The solution was added to 6-fluoro-1-(phenylsulfonyl)-1H-indol-5-ol (100 mg, 0.343 mmol; Intermediate 95) in EtOH (1 ml) and the mixture was heated in microwave oven at 90 oC for 10 min. Solvent was evaporated and 20% of material was purified on Gilson HPLC using 15-45% MeCN in 50 nM ammonium hydrogencarbonate buffer. Yield: 13 mg; white solid. MS (ESI+) for C18H19FN2O3S m/z 363 (M+H)+.

Workup

  1. customwas obtained
  2. temperaturethe mixture was heated in microwave oven at 90 oC for 10 min
  3. customSolvent was evaporated
  4. custom20% of material was purified on Gilson HPLC

Sources & evidence

ORD record
ord-b6912e261f6e41f990a282c45c18bcb4
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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