Formaldehyde → HCID 70208440, compound

HRID 611574Notes

Reaction equation

HRID 611574 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[CH:5]=[C:6]2[CH:12]=[C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][NH:14]3)[O: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[CH:12]=[C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[CH3:20])[O:10][C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 70208310HCID 70208310, compound

Product 1

HCID 70208440HCID 70208440, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 200 mg (0.80 mmol) sample of 5-chloro-2-(2-(S)-pyrrolidinyl)-furo[2,3-b]pyridine dihydrochloride, from Example 13c above, was dissolved in 4 mL of 88% formic acid and 8 mL of 37% aqueous formaldehyde and heated at reflux for 1 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 product was converted to the salt by treatment with HCl/ether to give 140 mg of title compound: 1H NMR (D2O, 300 MHz) δ 2.29-2.38 (m, 2H), 2.49-2.68 (m, 2H), 2.95 (br s, 3H), 3.44 (m, 1H), 3.84 (m, 1H), 4.84 (m, 1H), 7.22 (s, 1H), 8.22 (d, 1H, J=2.3 Hz), 8.36 (d, 1H, J=2.4); MS m/z: 237 (M+H)+, 254 (M+NH4)+ ; Anal. Calcd for C12H13N2OCl.1.0 HCl.0.3 H2O: C, 51.74; H, 5.28; N, 9.73. Found: C, 51.74; H, 5.28; N, 10.16.

Workup

  1. temperatureat reflux for 1 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

Sources & evidence

ORD record
ord-5acc097f0b2d4f439583f535fb49874f
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

Loading…