Formaldehyde → HCID 70207639, compound

HRID 611564Notes

Reaction equation

HRID 611564 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[CH:5]=[C:6]2[O:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][NH:14]3)=[CH:10][C:7]2=[N:8][CH:9]=1.C=O.[C:20]([O-])([O-])=O.[K+].[K+]>C(O)=O>[ClH:3].[ClH:1].[Cl:3][C:4]1[CH:5]=[C:6]2[O:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[CH3:20])=[CH:10][C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 70207845HCID 70207845, compound

Product 1

HCID 70207639HCID 70207639, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 315 mg (1.04 mmol) sample of 6-chloro-2-(2-(S)-pyrrolidinyl)-furo[3,2-b]pyridine dihydrochloride, from Example 7c above, was dissolved in 3 mL of 88% formic acid and 6 mL of 37% aqueous formaldehyde and heated at reflux for 0.5 hour. The reaction mixture was cooled, poured into saturated K2CO3, and the mixture was extracted with CH2Cl2. The extract was dried over MgSO4, and the solvent was removed. The residue was chromatographed on silica gel, eluting with 100:0 to 95:5 CHCl3 :MeOH. The residue was converted to the salt by treatment with HCl/ether, and the salt was recrystallized from ethanol/EtOAc to give 159 mg of title compound: 1H NMR (D2O, 300 MHz) δ 2.31-2.39 (m, 2H), 2.52-2.70 (m, 3H), 2.96 (br s, 3H), 3.55 (br s, 1H), 3.88 (br s, 1H), 7.33 (s, 1H), 8.13 (dd, 1H), 8.56 (d, 1H); MS m/z: 237 (M+H)+, 254 (M+NH4)+ ; Anal. Calcd for C12H13N2OCl.2HCl: C, 46.55; H, 4.88; N, 9.05. Found: C, 50.75; H, 5.12; N, 9.69.

Workup

  1. temperatureat reflux for 0.5 hour
  2. temperatureThe reaction mixture was cooled
  3. extractionthe mixture was extracted with CH2Cl2
  4. dry with materialThe extract was dried over MgSO4
  5. customthe solvent was removed
  6. customThe residue was chromatographed on silica gel
  7. washeluting with 100:0 to 95:5 CHCl3
  8. customthe salt was recrystallized from ethanol/EtOAc

Sources & evidence

ORD record
ord-3521591fdec841818ff1ce6ede5964fd
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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