Dimethylformamide → HCID 58014984, compound

HRID 1676527Notes

Reaction equation

HRID 1676527 reaction equation
Cl.Cl.[CH3:3][S:4]([CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]1)(=[O:6])=[O:5].N1([O:26][C:27](=O)[C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[C:30]([O:35][CH3:36])[CH:29]=2)C2C=CC=CC=2N=N1.CN(C)C=O.C(N(CC)CC)C>ClCCl>[NH2:34][C:31]1[CH:32]=[CH:33][C:28]([C:27]([NH:16][CH:13]2[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][CH2:7][S:4]([CH3:3])(=[O:6])=[O:5])[CH2:11][CH2:12]2)=[O:26])=[CH:29][C:30]=1[O:35][CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 106606854-Amino-3-methoxy-benzoic acid benzotriazol-1-yl esterHCID 673553041-(3-Methanesulfonyl-propyl)-piperidin-4-ylamine dihydrochloride

Product 1

HCID 58014984HCID 58014984, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2.3 g of 1-(3-methanesulfonyl-propyl)-piperidin-4-ylamine dihydrochloride, 2.7 g (0.0095 mole) of 4-amino-3-methoxy-benzoic acid benzotriazol-1-yl ester and 15 mL of dimethylformamide was added 4.0 g (0.0395 mole) of triethylamine. The mixture was stirred at room temperature for 20 hours, then diluted with 150 mL of dichloromethane. The mixture was washed twice with 100 mL of sodium bicarbonate, once with 50 mL of water, once with 50 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol (gradient, 100:0-80:20) to give 2.0 g of 4-amino-N-[1-(3-methanesulfonyl-propyl)-piperidin-4-yl]-3-methoxy-benzamide.

Workup

  1. washThe mixture was washed twice with 100 mL of sodium bicarbonate, once with 50 mL of water, once with 50 mL of brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with dichloromethane-methanol (gradient, 100:0-80:20)

Sources & evidence

ORD record
ord-e7c1cfcc53fb43d08405f509ec108626
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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