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Dimethylformamide → 4-amino-N-[1-(2,2-difluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamide

HRID 1676522
Notes
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Reaction equation

HRID 1676522 reaction equation
N1(O[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:19][CH3:20])[CH:13]=2)C2C=CC=CC=2N=N1.Cl.Cl.[F:24][CH:25]([F:34])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1.CN(C)C=O.C(N(CC)CC)C>ClCCl>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:33][CH:30]2[CH2:29][CH2:28][N:27]([CH2:26][CH:25]([F:34])[F:24])[CH2:32][CH2:31]2)=[O:21])=[CH:13][C:14]=1[O:19][CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 106606854-Amino-3-methoxy-benzoic acid benzotriazol-1-yl esterHCID 754807781-(2,2-Difluoroethyl)piperidin-4-amine dihydrochloride

Product 1

HCID 580151184-amino-N-[1-(2,2-difluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamideYield 88.6%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.07 g (3.78 mmole) of 4-amino-3-methoxy-benzoic acid benzotriazol-1-yl ester, 0.90 g (3.78 mmole) of 1-(2,2-difluoro-ethyl)-piperidin-4-ylamine dihydrochloride and 5 mL of dimethylformamide was added 2.63 mL of triethylamine. The mixture was stirred for 20 hours, then taken up in dichloromethane and washed twice with 100 mL of saturated aqueous sodium bicarbonate, once with 50 mL water, once with 50 mL 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, 100:0-90:10) to give 1.05 g of 4-amino-N-[1-(2,2-difluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamide.

Workup

  1. washwashed twice with 100 mL of saturated aqueous sodium bicarbonate, once with 50 mL water, once with 50 mL 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, 100:0-90:10)

Sources & evidence

ORD record
ord-934855b7942f4bdf8c6747753f11c246
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08003785B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes