3-Methoxypropylamine → HCID 58065585, compound

HRID 217791Notes

Reaction equation

HRID 217791 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[N:18][C:17]([NH2:20])=[C:16]([C:21](=[O:29])[NH:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[N:15]=2)=[CH:10][CH:9]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:36][O:37][CH2:38][CH2:39][CH2:40][NH2:41]>CC#N>[NH2:20][C:17]1[C:16]([C:21]([NH:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[O:29])=[N:15][C:14]([C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][NH:41][CH2:40][CH2:39][CH2:38][O:37][CH3:36])=[CH:13][CH:12]=2)=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 16723-MethoxypropylamineHCID 11430Potassium CarbonateHCID 86661489HCID 86661489, compound

Product 1

HCID 58065585HCID 58065585, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product of step (iv) (250 mg, 0.61 mmol), K2CO3 (250 mg, 1.8 mmol), 3-methoxypropylamine (82 mg, 0.92 mmol) in MeCN (20 mL, Aldrich, HPLC grade) was stirred at 90° C. under N2 atmosphere overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue subjected to prep-HPLC for purification, the eluents were concentrated and 1N NaOH solution added into the residue to control the pH=8˜9. The mixture was extracted with DCM three times. The combined extracts was dried over anhydrous sodium sulphate, filtered, concentrated in vacuo, which afforded the title compound (yellow solid, 158 mg)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customprep-HPLC for purification
  5. concentrationthe eluents were concentrated
  6. addition1N NaOH solution added into the residue
  7. extractionThe mixture was extracted with DCM three times
  8. dry with materialThe combined extracts was dried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo, which

Sources & evidence

ORD record
ord-e186131d8f2a415a896c16982e14b78c
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Reaction notes

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