Formaldehyde → HCID 59350823, compound

HRID 1644729Notes

Reaction equation

HRID 1644729 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH2:8]([O:10][C:11](=[O:41])[CH2:12][C:13]1[CH:22]=[C:21]([C:23](=[O:39])[C:24]2[CH:29]=[CH:28][C:27]([S:30]([N:33]3CCNCC3)(=[O:32])=[O:31])=[CH:26][CH:25]=2)[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:40])[CH:19]=2)[CH:14]=1)[CH3:9].C=O.C([BH3-])#N.[Na+]>C(#N)C.C(O)(=O)C>[CH2:8]([O:10][C:11](=[O:41])[CH2:12][C:13]1[CH:22]=[C:21]([C:23](=[O:39])[C:24]2[CH:25]=[CH:26][C:27]([S:30]([N:33]3[CH2:7][CH2:6][N:3]([CH3:1])[CH2:4][CH2:5]3)(=[O:32])=[O:31])=[CH:28][CH:29]=2)[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:40])[CH:19]=2)[CH:14]=1)[CH3:9]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 59350847HCID 59350847, compound

Product 1

HCID 59350823HCID 59350823, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

Triethylamine (0.04 mL, 0.27 mmol) was added to a stirred mixture of {6-fluoro-4-[4-(piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid ethyl ester (0.10 g, 0.17 mmol) in acetonitrile (4 mL) at 0° C. and the reaction mixture was stirred for 15 minutes. Formaldehyde (0.02 mL, 0.83 mmol) and sodium cyanoborohydride (0.017 g, 0.27 mmol) were added to the reaction mixture at 0° C., then the mixture was stirred for another 15 minutes. The reaction mixture was neutralized to pH ˜7 by gradual addition of acetic acid. The reaction mixture was concentrated, and the residue was made alkaline by the addition of a 2.0 N aqueous solution of KOH. The resulting mixture was extracted with diethyl ether (2×15 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. Silica gel (100-200 mesh) column chromatography (4:1 ethyl acetate-hexanes) afforded 0.05 g (60%) of {6-fluoro-4-[4-(4-methyl-piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid ethyl ester as an off-white sticky solid. MS cald. for C26H27FN2O5S ([M+H]+) 499, obsd. 499.3.

Workup

  1. stirringthe mixture was stirred for another 15 minutes
  2. concentrationThe reaction mixture was concentrated
  3. additionby the addition of a 2.0 N aqueous solution of KOH
  4. extractionThe resulting mixture was extracted with diethyl ether (2×15 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain the crude product

Sources & evidence

ORD record
ord-c82a69e9e92c4bb287747e322ea5efa7
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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