Methylamine → HCID 66823397, compound

HRID 2362181Notes

Reaction equation

HRID 2362181 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:23][N:22]4[N:31]=[C:32]([C:34]([OH:36])=O)[N:33]=[C:21]4[N:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN.C1C=CC2N(O)N=[N:45][C:43]=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[C:24]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:23][N:22]4[N:31]=[C:32]([C:34](=[O:36])[NH:45][CH3:43])[N:33]=[C:21]4[N:20]=3)=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66823367HCID 66823367, compound

Product 1

HCID 66823397HCID 66823397, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-3 (243 mg, 0.5 mmol) in DMF (5 mL) was added Methanamine HC salt (50 mg, 0.75 mmol), HOBT (73 mg, 0.5 mmol), EDCI (192 mg, 1 mmol) and TEA (125 mg, 1.25 mmol) at room temperature and the mixture was stirred for overnight. The mixture was diluted with 15 mL of H2O, extracted with EA, the combined organic phase was washed with NaHCO3 aq. and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.HPLC to give 8-7.

Workup

  1. extractionextracted with EA
  2. washthe combined organic phase was washed with NaHCO3 aq. and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep.HPLC
  6. customto give 8-7

Sources & evidence

ORD record
ord-179edbe7da7a4607b3ee1735861b8792
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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