Formaldehyde → HCID 67003867, compound

HRID 2362663Notes

Reaction equation

HRID 2362663 reaction equation
[Cl:1][C:2]1[C:3]([C:17]2[S:21][C:20]([C:22]3([O:26][CH2:27][O:28][CH3:29])[CH2:25][CH2:24][CH2:23]3)=[N:19][CH:18]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH2:30]=O.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>C(O)(=O)C>[Cl:1][C:2]1[C:3]([C:17]2[S:21][C:20]([C:22]3([O:26][CH2:27][O:28][CH3:29])[CH2:25][CH2:24][CH2:23]3)=[N:19][CH:18]=2)=[C:4]2[C:10]([CH2:30][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268Pyrrolidine2×HCID 67003455HCID 67003455, compound

Product 1

HCID 67003867HCID 67003867, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A solution of Example 47B (0.034 g, 0.079 mmol) in 0.8 mL acetic acid was treated with formalin (0.035 mL, 0.475 mmol) and pyrrolidine (0.039 mL, 0.475 mmol). The reaction was heated at 75° C. for 1 hour. Additional pyrrolidine (0.163 mL, 1.98 mmol) was added, and the reaction was heated at 75° C. for 6 hours. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The concentrate was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The aqueous layer was extracted with additional dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the title compound. ESI(+) m/z 513.1 [M+H]+.

Workup

  1. temperaturethe reaction was heated at 75° C. for 6 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe concentrate was dissolved in dichloromethane
  5. washwashed with saturated aqueous sodium bicarbonate
  6. extractionThe aqueous layer was extracted with additional dichloromethane
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a3591d07475b455fa1d8b6ecfbee7e20
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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